4-Nitrobenzenesulfonyl chloride → 3-((tert-Butyldimethylsilyl)oxy)propyl 4-nitrobenzenesulfonate

HRID 1594933노트

반응식

HRID 1594933 반응식
[O:1]([CH2:9][CH2:10][CH2:11][OH:12])[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].C(N(C(C)C)CC)(C)C.[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1)([O-:24])=[O:23].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:8][C:5]([Si:2]([O:1][CH2:9][CH2:10][CH2:11][O:12][S:31]([C:28]1[CH:27]=[CH:26][C:25]([N+:22]([O-:24])=[O:23])=[CH:30][CH:29]=1)(=[O:32])=[O:33])([CH3:4])[CH3:3])([CH3:6])[CH3:7]

참가 물질

6

반응물 4

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 40777913-[(Tert-butyldimethylsilyl)oxy]propan-1-ol

생성물 1

HCID 570160853-((tert-Butyldimethylsilyl)oxy)propyl 4-nitrobenzenesulfonate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 3-t-butlydimethylsiloxy-1-propanol, prepared by the method of McDougal, et al. JOC, 1986, 51, 3388, which is incorporated herein by reference, (7.6 g, 40 mmol) and diisopropylethylamine (10.4 mL, 60 mmol) in methylene chloride (200 mL) at 0° C. was treated with p-nitrophenylsulfonyl chloride (9.7 g, 44 mmol), stirred for 3 h, poured into saturated NaHCO3 and extracted with diethyl ether. The extracts were washed with brine, dried (Na2SO4), and concentrated. The residue was chromatographed on silica gel with 5% ethyl acetate/hexanes to provide 6.00 g of the title compound.

후처리

  1. extractionextracted with diethyl ether
  2. washThe extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel with 5% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-53453c790f80432898db7b6bac6350f6
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06284796B1

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