4-Toluenesulfonyl chloride → 6-Phenylhexyl tosylate

반응식

[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:14](Cl)([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15].CCN(CC)CC>CN(C1C=CN=CC=1)C>[S:14]([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)([O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:16])=[O:15]

참가 물질

실험 절차

This compound was synthesized as a colorless oil from 6-phenylhexan-1-ol (137.0 mg, 0.77 mmol), TsCl (190.7 mg, 1.00 mmol), Et3N (155.0 mg, 1.54 mmol), and DMAP (93.8 mg, 0.77 mmol) in 81% yield by following general procedure 1.1: 1H NMR (400 MHz, CDCl3, δH) 7.87-7.77 (m, 2H), 7.35 (d, J=8.0 Hz, 2H), 7.33-7.24 (m, 2H), 7.23-7.13 (m, 3H), 4.03 (t, J=6.5 Hz, 2H), 2.65-2.53 (m, 2H), 2.45 (s, 3H), 1.75-1.50 (m, 4H), 1.45-1.19 (m, 4H); 13C NMR (100 MHz, CDCl3, 144.93, 142.73, 133.40, 130.08, 128.60, 128.52, 128.11, 125.92, 70.89, 35.99, 31.44, 28.98, 28.78, 25.47, 21.88. ESI-MS: 333.1 (M+H+), 355.1 (M+Na+).