HCID 14802187, compound → HCID 14802188, compound

Participants

Reaction Steps

0.3 g of lithium aluminum hydride was suspended in 30 ml of tetrahydrofuran, and a solution of 1.7 g of 5-(5-hydroxy-4,6,7-trimethyl-1,3-benzoxathiole-2-yl)-2,2-dimethylpentanoic acid (prepared as described in Example 81) in 5 ml of tetrahydrofuran was added dropwise under a stream of nitrogen and with ice-cooling to the suspension. After the dropwise addition, the reaction mixture was kept at room temperature for 1 hour and was then heated under reflux for 2 hours. The reaction mixture was then poured into ice-water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate, after which the ethyl acetate was distilled off under reduced pressure. The resulting residue was subjected to silica gel Lobar column chromatography, and the title compound was obtained by elution with a 9:1 by volume mixture of benzene and ethyl acetate.

Provenance & Evidence