Dichloromethane → (4R)-3-[(2R,3S,4R,5S,6S,7Z)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[(4-methoxyphenyl)methoxy]-2,4,6-trimethyl-1-oxo-7,9-decadienyl]4-(phenylmethyl)-2-oxazolidinone

Participants

Reaction Steps

A solution of (4R)-3-[(2R,3S,4S,5S,6S,7Z)-3-hydroxy-5-[(4-methoxyphenyl)methoxy]-2,4,6-trimethyl-1-oxo-7,9-decadienyl]-4-(phenylmethyl)-2-oxazolidinone (3.4 g, 6.53 mmol), 2,6-lutidine (3.5 g, 32.65 mmol) and methylene chloride (100 mL) is cooled to 0° C. TBSOTf (7.12 g, 26.94 mmol)is added over 30 min and the resultant mixture is allowed to react overnight at 0° C. The mixture is diluted with ether (300 mL), washed with aqueous NaHSO4, brine, and concentrated. Flash chromatography affords the desired compound (3.6 g, 87%) as an oil.

Provenance & Evidence