[CH2:1]1[C:6]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][C:3](=O)[CH2:2]1.S([CH2:23][N+:24]#[C-])(C1C=CC(C)=CC=1)(=O)=O.CCO.CC([O-])(C)C.[K+]>COCCOC>[CH2:1]1[C:6]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][CH:3]([C:23]#[N:24])[CH2:2]1
To a solution of spiro[5.5]undecan-3-one (1.66 g, 10 mmol) and tosylmethylisocyanide (2.54 g, 13 mmol) in DME (50 ml) and abs. EtOH (1 ml) was added KOtBu (2.69 g, 24 mmol) portionwise during 0.5 hr at −10° C. After addition, the reaction mixture was stirred at 0° C. for 1 hr then 2 hr at ambient temperature. Solvent was removed in vacuo and the resulting residue was extracted with diethyl ether (50 ml×3) and the combined organic layer was washed with water (50 ml ×3). The organic layer was dried with anhydrous MgSO4, concentrated under reduced pressure and purified by flash column chromatography (50% -100% CH2Cl2/Hexane) to give the nitrile as colorless solid (1.28 g, 72% Yield). 1H-NMR (360 MHz, CDCl3) δ 2.58-2.53 (m, 1H), 1.83-1.70 (m, 4H), 1.63-1.58 (m, 2H), 1.40-1.26 (m, 8H), 1.28-1.20 (m, 4H); 13C-NMR (90 MHz, CDC13) δ 122.79, 34.41, 31.88, 28.37, 26.88, 24.73, 21.64, 21.55; ESI-MS: Calculated for C12H19N (M+H)+ 178.3, Found: 178.2.
Wird geladen…
