Tetrahydrofuran → 2-(1,3-Dioxaindan-5-yl)ethan-1-ol

Participants

Reaction Steps

A solution of 3,4-(methylenedioxy)phenylacetic acid (Intermediate D1) (commercially available from Aldrich) (2 g, 11 mmol) in diethyl ether (40 mL) and THF (60 mL) was treated with lithium aluminum hydride: LiAlH4 (24 mL, 1 M in ether) at rt for 16 h. Rochelle's salt solution was added to quench the reaction mixture. The aqueous layer was extracted with ether (3×100 mL). The combined organic fractions were dried over MgSO4, filtered and evaporated to give 1.8 g of 2-benzo[1,3]dioxol-5-yl-ethanol (Intermediate D2) that was sufficiently pure to be used in the next synthetic step.

Provenance & Evidence