[H-].[Na+].[F:3][C:4]1[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=1[CH2:6][CH:7]1[CH2:12][CH2:11][CH:10]([CH2:13][OH:14])[CH2:9][CH2:8]1.[F:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24](F)[C:21]=1[C:22]#[N:23]>CN(C)C=O>[F:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([O:14][CH2:13][CH:10]2[CH2:9][CH2:8][CH:7]([CH2:6][C:5]3[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=3[F:3])[CH2:12][CH2:11]2)[C:21]=1[C:22]#[N:23]In an 18 mL vial, sodium hydride was suspended in 2 mL dry dimethylformamide and chilled to 0° C. under nitrogen flow. 4-(2-Fluorobenzyl)cyclohexylmethanol (155 mg; 0.7 mmol) was added over 2 minutes and warmed to room temperature for 2 hours. Mixture was then added to a 0° C. mixture of 2,6-difluorobenzonitrile (97 mg; 0.7 mmol) in 2 mL of dimethylformamide over 1 minute and mixture continued to stir an additional 2 hours. Mixture was quenched over 10 g of ice and extracted 3× ethyl acetate 20 mL each. Combined organics were washed 5× water, brine and dried over MgSO4. Colorless oil was obtained and purified by flash chromatography (20:1) with 0-5% ethyl acetate in hexanes to give 233 mg of title compound. (98% yield).
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