Triphenylphosphine → 4-(2-((1-((tert-butyldiphenylsilyl)methoxy)cyclopropyl)methoxy)-3,4-dimethoxyphenyl)-2,3-dihydro-1H-inden-1-one

Participants

Reaction Steps

To a stirring solution of 4-(2-hydroxy-3,4-dimethoxy-phenyl)-indan-1-one (Compound 303) (5 g, 17.60 mmol) in tetrahydrofuran (50 mL), were added triphenylphosphine (9.2 g, 35.21 mmol) and diisopropylazodicarboxylate (7.11 g, 35.21 mmol) and {1-[(tert-Butyl-diphenyl-silanyl)-methoxy]-cyclopropyl}-methanol (7.18 g, 21.12 mmol) and the resultant reaction mixture was stirred at RT for 2 h. The reaction mixture was quenched with water and extracted with ethyl acetate (3×). The combined ethyl acetate layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification by column chromatography (silica gel, 0-10% ethyl acetate in pet ether) afforded 4-(2-((1-((tert-butyldiphenylsilyl)methoxy)cyclopropyl)methoxy)-3,4-dimethoxyphenyl)-2,3-dihydro-1H-inden-1-one as a liquid.

Provenance & Evidence