4-Hydroxy-1,7-bis(tert-butyldiphenylsilyloxy)heptane → 1,7-Bis(tert-butyldiphenylsilyloxy)heptan-4-one

Participants

Reaction Steps

A solution of 49 (233 mg, 0.374 mmol) in CH2Cl2 (1 mL) was treated with PCC (121 mg, 0.561 mmol) at room temperature. Stirring was continued for 2 h. The mixture was diluted with Et2O, and the mixture was applied onto a plug of silica. The solid was washed with Et2O. The sample was concentrated, and the oily residue was chromatographed [silica, hexanes/ethyl acetate (10:1) to yield a colorless oil (166 mg, 71%): 1H NMR δ 1.82-1.88 (m, 4H), 2.55-2.58 (m, 4H), 3.65-3.72 (m, 4H), 7.43-7.45 (m, 12), 7.69-7.71 (m, 8H).

Provenance & Evidence