Protection of Acetol as THP ether

Protection of Acetol as THP ether

 

Protection of Acetol as THP ether

 

Literature References

1. Xiao, Y.; Liu, P. Angew. Chem. Int. Ed. 2008, 47, 9722-9725.
   • See the supplemental material for a "Synthesis of acetonyl tetrahydropyranyl ether (17)".
2. Sondheimer, F.; Stjernstrom, N.; Rosenthal, D. J. Org. Chem. 1959, 24, 1280-1284.
   • Look for the experimental for "Acetol 2'-tetrahydropyranyl ether (VIIIb)". Interestingly, they say that the material was stored at -10 degrees C, or used directly for the next step since it decomposed on standing at room temperature!
3. Hagiwara, H.; Uda, H. J. Chem. Soc., Perkin-I 1984, 91.

  The literature listing for the NMR (Xiao reference above) is ¹H-NMR (CDCl₃, 400 MHz): 4.64 (t, J = 3.6 Hz, 1 H), 4.26 (d, J = 17.6 Hz, 1 H), 4.12 (d, J = 17.6 Hz, 1 H), 3.81-3.86 (m, 1 H), 3.49-3.54 (m, 1 H), 2.18 (s, 3 H), 1.61-1.89 (m, 6 H).

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