[C:1]1([C:11]2([CH2:16]OS(C)(=O)=O)[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C-:22]#[N:23].[Na+].C(OCC)(=O)C>CS(C)=O.CCCCCC>[C:1]1([C:11]2([CH2:16][C:22]#[N:23])[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1To a stirred solution of methanesulfonic acid 1-naphthalen-1-yl-cyclopentylmethyl ester (341) (2.1 g, 6.90 mmol) in dimethyl sulfoxide (10.0 mL) were added KI (115 mg, 0.69 mmol) and NaCN (507 mg, 10.35 mmol) and the reaction mixture was stirred at 140° C. for 2 h (silica TLC, 10% ethyl acetate in hexane; Rf=0.5). The reaction mass was cooled to room temperature, quenched with FeSO4 solution (15 mL) and diluted with water (100 mL). The resulting solid was separated through filtration and washed well with ethyl acetate. The biphasic layer was separated in a separating funnel. The organic part was washed with brine (2×50 mL), dried and concentrated in vacuo to get a crude mass which was purified by Combi-Flash using a mixture of ethyl acetate and hexane as gradient eluent to get pure (1-naphthalen-1-yl-cyclopentyl)-acetonitrile (342) (710 mg, 44%) as a yellow gummy liquid.
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