Water → Ethyl (6-methoxyindan-1-yl)acetate

Participants

Reaction Steps

To a suspension of 60% sodium hydride (1.84 g, 46.0 mmol) in THF (200 ml) was added dropwise, under ice-cooling, triethyl phosphonoacetate (10.3, g, 46.0 mmol). The mixture was stirred until the reaction mixture became a homogeneous solution. To the solution was added a suspension of 6-methoxy-1-indanone (7.10 g, 43.8 mmol) in THF (30 ml). The mixture was stirred for 2 hours at room temperature and for further 12 hours at 70° C. To the reaction mixture was added water, which was subjected to extraction with ethyl acetate. The extract solution was washed with brine, which was dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The concentrate was dissolved in ethanol (200 ml), to which was added 5% Pd-C (50% hydrous, 2.5 g). The mixture was stirred for 1.5 hours at 50° C. under hydrogen atmosphere. The reaction mixture was subjected to filtration, and the filtrate was concentrated under reduced pressure. The concentrate was purified by means of a silica gel column chromatography (hexane/ethyl acetate, 97:3→4:1) to give 6.55 g (yield 64%) of the above-titled compound as an oily product.

Provenance & Evidence