Methyl 2-(4-oxochroman-3-yl)acetate

 Methyl 2-(4-oxochroman-3-yl)acetate

1H NMR (500 MHz, CDCl₃):

δ = 2.44 (dd, J = 17.0, 8.1 Hz, 1H), 

2.95 (dd, J = 17.0, 5.0 Hz, 1H), 

3.31-3.37 (m, 1H), 3.74 (s, 3H), 

4.30 (dd, J = 12.0, 11.2 Hz, 1H), 

4.60 (dd, J = 11.2, 5.3 Hz, 1H), 

6.98 (d, J = 8.4 Hz, 1H), 

7.03 (apparent triplet, J = 7.5 Hz, 1H), 

7.48 (apparent triplet, J = 8.4 Hz, 1H), 

7.89 (d, J = 7.8 Hz, 1H)

13C NMR (125 MHz, CDCl₃): δ = 30.1, 42.5, 52.0, 70.2, 117.8, 120.4, 121.5, 127.3, 136.0, 161.7, 171.8(C=0), 192.5(C=0)

GC-MS: (EI) 220 (M+, 2%), 189 (17), 147 (100), 120 (58), 92 (33)

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References

Yoshikai, K.; Hayama, T.; Nishimura, K.; Yamada, K.; Tomioka, K. J. Org. Chem., 2005, 70, 681-683.
Santoso, H.; Casana, M. I.; Donner, C. D. Org. Biomol. Chem., 2014, 12, 171-176.

1. Roberts, B. P. Chem. Soc. Rev., 1999, 28, 25-35.

2. Aitken, H. M.; Schiesser, C. H.; Donner, C. D. Aust. J. Chem., 2011, 64, 409-415.