Triphenylphosphine → 2-Phenylthiomethylsaccharin

HRID 129044

Reaction equation

HRID 129044 reaction equation
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

Participants

5

Reactant 3

HCID 11776Triphenylphosphine2×HCID 121412-(Benzyloxy) ethanolHCID 103166544-Isopropyl-6-hydroxy-2-phenylthiomethylsaccharin

Product 1

HCID 545645412-Phenylthiomethylsaccharin

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was purified by column chromatography on silica eluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-1ed5eb1f820842b8866e4feeb20955ce
Source dataset
uspto-grants-1995_11
Patent number
US05466701

Linked notes

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