Phosphorus oxychloride → HCID 86753269, compound

Participants

Reaction Conditions

Reaction Steps

1.43 g (4.58 mmol) of (S)-1-[(1S,3aR,4S,7aR)-4-(tert-Butyldimethyl-silanyloxy)7a-methyl-octahydro-inden-1-yl]ethanol was dissolved in 15 ml pyridine and cooled to 0° C. 420 μl of POCl3 were added slowly. The reaction mixture was stirred at room temperature overnight then poured into a buffer at pH 4, extracted with n-hexane. The organic solution was washed with brine, dried over sodium sulfate and evaporated to dryness. The residue was purified by column chromatography (eluent: n-hexane) to yield 516 mg (39%) of (E)-(3aR,4S,7aS)-4-(tert-Butyl-dimethyl-silanyloxy)-1-ethylidene-7a-methyl-octahydro-indene (E)-(3aR,4S,7aS)-4-(tert-Butyldimethyl-silanyloxy)-1-ethylidene-7a-methyl-octahydro-indene as a colourless oil.

Provenance & Evidence