Dimethyl Sulfoxide → (2R,3S,4S,5Z)-3-[(4-methoxyphenyl)methoxy]-2,4-dimethyl-5,7-octadienal

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Reaction Steps

A solution of (2S,3S,4S,5Z)-3-[(4-methoxyphenyl)methoxy]-2,4-dimethyl-5,7-octadien-1-ol (2.0 g, 6.9 mmol), DMSO (2.1 mL), NEt3 (2.79 g, 27.59 mmol) and methylene chloride (20 mL) is cooled to 0° C., and is treated with SO3-Pyr (3.29 g, 20.69 mmol) and DMSO (8 mL) over 10 min. After additional 2 h at 0° C., the mixture is diluted with ether (200 mL), washed with 1 M aqueous NaHSO4 (100 mL), brine (100 mL), and concentrated. Flash chromatography (1% to 10% ethyl acetate in hexane) gives the desired compound (1.95 g, 98.2%) as a colorless oil.

Provenance & Evidence