Propylene Oxide → HCID 22612707, compound

Participants

Reaction Steps

To a stirred suspension of sodium hydride (60%, 1.26 g, 31.6 mmol) in tetrahydrofuran (30 mL) at 0° C. under Ar was added dropwise a solution of 6-chloroindole (4.0 g, 26 mmol) in tetrahydrofuran (30 mL). The mixture was stirred for 1 h and (RS)-propylene oxide (3.7 mL, 53 mmol) was added. The mixture was warmed to room temperature, stirred for 48 h and partitioned between aqueous ammonium chloride solution (100 mL) and ether (3×100 mL). The combined organic extracts were washed with brine (2×100 mL), dried (magnesium sulfate), concentrated in vacuo and purified by column chromatography [SiO2; ethyl acetate-hexane (1:9)] to give the product (2.78 g, 50% yield) as a pale yellow oil. Data for the compounds produced using General Method A, step (a) are listed in Table 3.

Provenance & Evidence