Triphenylphosphine → 2-Phenylthiomethylsaccharin

HRID 129044

Reaktionsgleichung

Reaktionsgleichung von HRID 129044
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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 545645412-Phenylthiomethylsaccharin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-1ed5eb1f820842b8866e4feeb20955ce
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05466701

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