Triphenylphosphine → 2-Phenylthiomethylsaccharin

反応式

O[C:2]1[CH:12]=[C:11]2[C:5]([C:6](=[O:21])[N:7]([CH2:13][S:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[S:8]2(=[O:10])=[O:9])=[C:4](C(C)C)[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCCO)C1C=CC=CC=1>C1COCC1>[C:15]1([S:14][CH2:13][N:7]2[C:6](=[O:21])[C:5]3[C:11](=[CH:12][CH:2]=[CH:3][CH:4]=3)[S:8]2(=[O:10])=[O:9])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

参加物

実験手順

To a solution of 6-hydroxy-4-isopropyl-2-phenylthiomethylsaccharin (2.0 g, 5.5 mol) in THF (40 mL) were added triphenylphosphine (1.46 g, 5.56 mmol), 2-benzyloxyethanol (0.87g, 5.71 mmol) and triphenylphosphine (0.99 g, 5.68 mmol). The mixture was stirred at room temperature for 16 hours, the solvent was removed in vacuo and the residue was purified by column chromatography on silica eluting with 20% EtOAc/hexane to afford 2.1 g (77%) of 4-isopropyl-6-[2-benzyloxy)ethoxy]-2-phenylthiomethylsaccharin, m.p. 98°-99° C.