4,4,5,5-tetramethyl-2-phenethyl-1,3,2-dioxaborolane

http://orgsyn.org/demo.aspx?prep=v94p0234

 4,4,5,5-Tetramethyl-2-phenethyl-1,3,2-dioxaborolane (1) has the following physical and spectroscopic properties: R_f = 0.47 (3:97, ethyl acetate:pentane), the checkers report the following values for 1: R_f = 0.09 (3:97 ethyl acetate:pentane); R_f = 0.52 (10% EtOAc in hexanes); Merck silica gel 60 F254 plate; mp 38-39 °C; 

¹H NMR pdf(CDCl₃, 400 MHz) δ: 1.18 (t, J = 8.4 Hz, 2H), 1.26 (s, 12H), 2.79 (t, J = 8.0 Hz, 2H), 7.16-7.22 (m, 1H), 7.23-7.32 (m, 4H); 

¹³C NMR pdf(CDCl₃, 151 MHz) d: 25.0, 30.1, 83.2, 125.6, 128.1, 128.3, 144.6 [N.B. the carbon attached to boron was not observed due to quadrupolar relaxation]; 

HRMS (ESI⁺) calculated for C₁₄H₂₂BO₂⁺ = 233.1707, mass found = 233.1710; 

IR (film): 3026, 2978, 2929, 1372, 1318, 1139, 848, 755, 703 cm^-1; 

Anal. calcd for C₁₄H₂₁BO₂: C, 72.44; H, 9.12. Found: C, 72.18; H, 9.28. 

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BRUSH UP YOUR NMR, 4-(3,5-Dichloropyridin-4-yl)morpholine

3,5-Dichloro-4-morpholinopyridine

Preparation of 4-(3,5-Dichloropyridin-4-yl)morpholine (5).(Pichowicz, M.; Crumpler, S.; McDonald, E.; Blagg, J. Tetrahedron 2010, 66, 2398, DOI: 10.1016/j.tet.2010.01.101)

 

 5 as a light-orange solid.

 

1H NMR (CDCl3, 400 MHz): δ = 8.35 (2H, s), 3.84 (4H, m), 3.37 (4H, m);

 

13C NMR (CDCl3, 101 MHz): δ = 150.8, 149.3, 128.4, 67.4, 50.4;

 

HRMS–ESI+: m/z [M + H]+ calcd for C9H11Cl2N2O+: 233.02429; found: 233.02446.

 

 

 

Org. Process Res. Dev., Article ASAP

DOI: 10.1021/acs.oprd.8b00009

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Clc2cncc(Cl)c2N1CCOCC1

METHYL 2-(ACETYLTHIO)ACETATE

Methyl 2-(methylthio)acetate

• Molecular FormulaC4H8O2S
• Average mass120.170 Da
• 16630-66-3
• S-Methylthioglycolate

DOI: 10.1021/acs.oprd.7b00378

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This paper demonstrates an efficient, mild, and chemoselective synthesis of various thioesters via a HOTf-catalyzed S-acetylation of aromatic and aliphatic thiols using isopropenyl acetate as a cheap and convenient acetylating agent. During our tests, we also investigated the differences between the activities of metal triflates and triflic acid as catalysts in the acetylation of thiols. Finally, the potential of our concept has been increased by the implementation of Nafion as a heterogeneous catalyst for S-acetylation of thiols.

S-Acetylation of Thiols Mediated by Triflic Acid: A Novel Route to Thioesters

Krzysztof Kuciński*  and Grzegorz Hreczycho* 

Faculty of Chemistry, Adam Mickiewicz University in Poznań, ul. Umultowska 89b, 61-614 Poznań, Poland

Org. Process Res. Dev., Article ASAP

DOI: 10.1021/acs.oprd.7b00378

Publication Date (Web): March 12, 2018

Copyright © 2018 American Chemical Society

*E-mail: kucinski.k@amu.edu.pl., *E-mail: g.h@amu.edu.pl. Web: http://ghgroup.home.amu.edu.pl.

 

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Concise synthesis of ketoallyl sulfones through an iron-catalyzed sequential four-component assembly

 

Concise synthesis of ketoallyl sulfones through an iron-catalyzed sequential four-component assembly

Green Chem., 2018, 20,973-977
DOI: 10.1039/C7GC03719H, Communication

Fuhong Xiao, Chao Liu, Dahan Wang, Huawen Huang, Guo-Jun Deng
A three starting material four component reaction (3SM-4CR) strategy is described to prepare [small beta]-acyl allylic sulfones from methyl ketones, sodium sulfinates and dimethylacetamide (DMA) in an iron-catalyzed oxidative system.

Concise synthesis of ketoallyl sulfones through an iron-catalyzed sequential four-component assembly

 

Fuhong Xiao,*^a  Chao Liu,^a  Dahan Wang,^a  Huawen Huang^a  and  Guo-Jun Deng*^a 

Author affiliations

* Corresponding authors

^a Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, Key Laboratory for Green Organic Synthesis and Application of Hunan Province, College of Chemistry, Xiangtan University, Xiangtan 411105, China
E-mail: fhxiao@xtu.edu.cn, gjdeng@xtu.edu.cn

Abstract

A three starting material four component reaction (3SM-4CR) strategy is described to prepare β-acyl allylic sulfones from methyl ketones, sodium sulfinates and dimethylacetamide (DMA) in an iron-catalyzed oxidative system. In this process, DMA was used as a dual synthon to provide two carbons. A broad range of functional groups were tolerated in this reaction system.

 1-phenyl-2-(tosylmethyl)prop-2-en-1-one (3ab)

 

43.2 mg, 72% yield).

 

1 H NMR (400 MHz, CDCl3) δ 7.78 (d, J = 8.2 Hz, 2H), 7.68-7.65 (m, 2H), 7.55 (t, J = 7.4 Hz, 1H), 7.43 (t, J = 7.8 Hz, 2H), 7.30 (d, J = 8.3 Hz, 2H), 6.25 (s, 1H), 6.02 (s, 1H), 4.35 (s, 2H), 2.39 (s, 3H).

 

13C NMR (100 MHz, CDCl3) δ 194.7, 144.9, 136.1, 135.8, 135.7, 133.9, 132.6, 129.8, 129.6, 128.3, 128.2, 57.7, 21.6.

 

HRMS calcd. for: C17H17O3S+ [M+H]+ 301.08929, found 301.08908

 

 

1H NMR PREDICT

13C NMR PREDICT ABOVE

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Cc1ccc(cc1)S(=O)(=O)CC(=C)C(=O)c2ccccc2