[H-].[Na+].[CH:3]1([OH:8])[CH2:7][CH2:6][CH2:5][CH2:4]1.F[C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1>O1CCOCC1>[CH:3]1([O:8][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1Suspend sodium hydride (336 mg, 2.8 mmol, 60% suspension in mineral oil) in anhydrous 1,4-dioxane (10 mL) under nitrogen atmosphere. Add cyclopentanol (620 mg, 7.2 mmol) and stir the resulting solution for 30 min. Add the preformed solution (3.35 mL, 2.4 mmol) to neat 4-fluorobenzonitrile (240 mg, 2 mmol) in a microwave tube and heat the sealed mixture at 100° C. for 30 min. Cool to room temperature and concentrate in vacuo. Purify by chromatography on silica gel eluting with isohexane/EtOAc (95:5 to 1:1 gradient) to obtain the desired intermediate (300 mg, 80%). GC-MS m/z: 187 (M+).
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