Methoxymethyl-triphenylphosphonium chloride → 1024683-61-1

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of methoxymethyl triphenylphosphonium chloride (13.8 g, 40 mmol) in dry THF (80 ml) is added dropwise a solution of lithium diisopropylamide (24.4 ml, 44 mmol, 1.8 M in hexane/THF/ethylbenzene), at 0-5° C. The resulting reaction mixture is stirred for 30 minutes and then cooled to −78° C. At this temperature, a solution of 4-benzyloxy-cyclohexanone (6.1 g, mmol) in tetrahydrofuran (30 ml) is added over a period of 30 minutes. Once the addition is completed the reaction mixture is stirred at −78° C. for 1 hour and then allowed to warm to room temperature and stirred overnight. The reaction mixture is then diluted to pH=2 with a 2N aqueous solution of hydrochloric acid and stirred for 3 hours at room temperature. The reaction was diluted with water and extracted with ethyl acetate (2×100 ml). The combined organic extracts are dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residue is purified by flash chromatography to give 4-benzyloxy-cyclohexanecarbaldehyde (5.7 g).

Provenance & Evidence