Triphenylphosphine → 2-Phenylthiomethylsaccharin

HRID 1768702Notes

Reaction equation

HRID 1768702 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 (0.87 g, 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-e72080348be040bc8550670a5fd81623
Source dataset
uspto-grants-1995_01
Patent number
US05378720

Reaction notes

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