Sodium Hydroxide → 3-Cyclopentylpropiolonitrile

To a solution of cyclopentylacetylene (0.50 g, 5.3 mmol) in THF (5 mL) at −78° C. was added 2.5 M n-butyllithium in hexane (2.23 mL). The mixture was stirred for 15 min followed by the dropwise addition of phenyl cyanate (0.70 g, 5.8 mmol) in THF (3 mL). The reaction was warmed to room temperature. Into the reaction mixture was poured 6 N NaOH, and the mixture was stirred for 5 minutes. The product was extracted with diethyl ether. The extracts were washed with 6 N NaOH and with brine, then dried over sodium sulfate, decanted and the solvent was removed in vacuo to afford product (600 mg, 95%). 1H NMR (300 MHz, CDCl3): δ □2.81-2.68 (m, 1H), 2.07-1.54 (m, 8H).

1. stirringthe mixture was stirred for 5 minutes
2. extractionThe product was extracted with diethyl ether
3. washThe extracts were washed with 6 N NaOH and with brine
4. dry with materialdried over sodium sulfate
5. customdecanted
6. customthe solvent was removed in vacuo

ORD record

ord-31708011e6de4685b81edc0bc4209d65

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08530485B2