2-cyclopentyloxy-5-formylbenzonitrile

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of cyclopentanol (1.15 g, 0.013 mol), in DMF (50 ml) was cooled to 0° C. Sodium hydride (1.54 g, 0.016 mol) was added portionwise to the solution and the mixture stirred at 0° C. for 10 minutes after complete addition. 3-Cyano-4-fluorobenzaldehyde (commercial) (2.0 g, 0.013 mol) was then added and the mixture allowed to warm to room temperature and stirred overnight. The reaction mixture was cooled to 0° C. and brine was added, the mixture was diluted with ethyl acetate (˜25 ml) and partitioned, the organic layer was washed with water (˜30 ml) and passed through a phase separating cartridge to dry. The solution was concentrated in vacuo and the residue purified by Biotage SP4, 40M with 20-60% ethylacetate/hexane as eluant. The product containing fractions were concentrated in vacuo to yield the title compound (1.02 g, 4.2 mmol) as a yellow liquid. MS (ES): requires C13H13NO2 215; found 216 (MH+). after complete addition to warm to room temperature stirred overnight The reaction mixture was cooled to 0° C. partitioned the organic layer was washed with water (˜30 ml) separating cartridge to dry The solution was concentrated in vacuo the residue purified by Biotage SP4, 40M with 20-60% ethylacetate/hexane as eluant The product containing fractions were concentrated in vacuo