Water → HCID 11418746, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2S,7S)-trans-2-isopropyl-7-[4-methoxy-3-(3-methoxypropoxy)-benzoyl]-8-methylnon-4-enoic acid (1.4 g; 3.2 mmol) in 1,2-dichloroethane were added triethylsilane (3.7 g; 32 mmol) and boron trifluoride diethyl etherate (2.7 g; 19.2 mmol), and the solution was stirred at 33° C. for 3 days. The reaction mixture was added to water and the aqueous layer was extracted 3× with tert-butyl methyl ether. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The remaining residue was purified by flash chromatography (silica gel; hexane/acetone 4:1) to obtain (2S,7R)-trans-2-isopropyl-7-[4-methoxy-3-(3-methoxypropoxy)benzyl]-8-methylnon-4-enoic acid (0.97 g, 2.3 mmol, 72% yield).

Provenance & Evidence