C([Li])CCC.[S:6]1[CH2:10][CH2:9][S:8][CH:7]1[C:11]([O:13][CH2:14][CH3:15])=[O:12].Br[CH2:17][CH2:18][CH2:19][C:20]#[N:21]>C1COCC1.C(OCC)C>[C:20]([CH2:19][CH2:18][CH2:17][C:7]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[S:8][CH2:9][CH2:10][S:6]1)#[N:21]n-Butyllithium (6.5 mL, 1.6 M in hexane) was added to a solution of ethyl 1,3-dithiolane-2-carboxylate (1925 mg, 10 mmol) in THF (10 mL) at −78° C. under N2. The reaction mixture was stirred for 30 min at −78° C. and then 4-bromobutanenitrile (1469 mg, 10 mmol) in THE (10 mL) was added. The mixture was warmed to room temperature and stirred for 30 min. It was diluted with diethyl ether and washed with 1 N HCl and H2O, and dried. Evaporation and purification by column chromatography afforded ethyl 2-(3-cyanopropyl)-1,3-dithiolane-2-carboxylate: LCMS tR=1.86 Min (5 min run, UV254nm), Mass calculated for, M+259.0, observed LC/MS m/z 260.0 (M+H).
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