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Ammonium Chloride → [5-({[Tert-butyl(diphenyl)silyl]oxy}methyl)-1,3,4-thiadiazol-2-yl]methanol

HRID 1881931
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HRID 1881931 반응식
[Si:1]([O:18][CH2:19][C:20]1[S:24][C:23]([C:25](OCC)=[O:26])=[N:22][N:21]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[Si:1]([O:18][CH2:19][C:20]1[S:24][C:23]([CH2:25][OH:26])=[N:22][N:21]=1)([C:14]([CH3:15])([CH3:16])[CH3:17])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1
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참가 물질

5

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HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 59331459Ethyl 5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-1,3,4-thiadiazole-2-carboxylate

생성물 1

HCID 59331609[5-({[Tert-butyl(diphenyl)silyl]oxy}methyl)-1,3,4-thiadiazol-2-yl]methanol수율 82%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

To a solution of ethyl 5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-1,3,4-thiadiazole-2-carboxylate (998 mg) in methanol (12 ml) was added sodium borohydride (177 mg), and the mixture was stirred at 0° C. for 1 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the title compound (738 mg, yield 82%) was obtained as a colorless amorphous solid from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-3cf3a1b9ad7d417c95007e5385708462
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08318746B2

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