Triphenylphosphine → 4-Isopropyl-6-[2-(triisopropylsilyloxy)ethoxy]-2-phenylthiomethylsaccharin

HRID 129045노트

반응식

HRID 129045 반응식
[CH:1]([C:4]1[CH:14]=[C:13]([OH:15])[CH:12]=[C:11]2[C:5]=1[C:6](=[O:24])[N:7]([CH2:16][S:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[S:8]2(=[O:10])=[O:9])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:44]([Si:47]([CH:55]([CH3:57])[CH3:56])([CH:52]([CH3:54])[CH3:53])[O:48][CH2:49][CH2:50]O)([CH3:46])[CH3:45].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH:1]([C:4]1[CH:14]=[C:13]([O:15][CH2:50][CH2:49][O:48][Si:47]([CH:52]([CH3:53])[CH3:54])([CH:44]([CH3:46])[CH3:45])[CH:55]([CH3:56])[CH3:57])[CH:12]=[C:11]2[C:5]=1[C:6](=[O:24])[N:7]([CH2:16][S:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[S:8]2(=[O:10])=[O:9])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 103166544-Isopropyl-6-hydroxy-2-phenylthiomethylsaccharinHCID 120121722-(Triisopropylsilyloxy) ethanol

생성물 1

HCID 699595524-Isopropyl-6-[2-(triisopropylsilyloxy)ethoxy]-2-phenylthiomethylsaccharin수율 86%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-isopropyl-6-hydroxy-2-phenylthiomethylsaccharin.(2.0 g, 5.509 mmol) in THF (35 mL) containing triphenylphosphine (1.59 g, 6.06mmol) and 2-(triisopropylsilyloxy) ethanol (1.13 g, 6.0 mmol) at room temperature was added diethylazodicarboxylate (1.04 mL, 6.6 mmol). The mixture was stirred overnight (16 hours), the solvent was removed in vacuo and the residue was purified by column chromatography on silica eluting with 10% ethyl acetate/hexane to afford 2.66 g (86%)of 4-isopropyl-6-[2-(triisopropylsilyloxy)ethoxy]-2-phenylthiomethylsaccharin as an oil

후처리

  1. customthe solvent was removed in vacuo
  2. customthe residue was purified by column chromatography on silica eluting with 10% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-234390b9d680494eb5092b36adef32af
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05466701

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