Sodium Hydroxide → 2-Benzo[b]thiophen-5-yl-3-cyclopentyl-propionitrile

Participants

Reaction Steps

In a round bottom flask was placed benzo[b]thiophen-5-yl-acetonitrile (700 mg, 4.04 mmol), tetrabutyl ammonium hydrogen sulfate (1.37 g, 4.04 mmol) and a 47% by weight solution of aqueous sodium hydroxide (646 μl, 8.08 mmol). To this well stirred mixture was added iodomethylcyclopentane (prepared in PCT WO 2004/052869 A1 Example 1, 1.69 g, 8.08 mmol) and the vigorously stirred mixture was heated to reflux for 6 h. The reaction was then diluted with water (5 mL) and methylene chloride (10 mL) and extracted with methylene chloride (3×20 mL). The organics were combined and dried over sodium sulfate, filtered and concentrated in vacuo. Purification an AnaLogix Intelliflash system (40 g column, 3% ethyl acetate/hexanes to 5% ethyl acetate/hexanes) afforded 2-benzo[b]thiophen-5-yl-3-cyclopentyl-propionitrile (416 mg, 40%) as a yellow oil: ES-HRMS m/e calcd for C16H17NS (M+H)+ 256.115, observed 256.115.

Provenance & Evidence