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

HRID 1594933ノート

反応式

HRID 1594933 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-53453c790f80432898db7b6bac6350f6
出典データセット
uspto-grants-2001_09
特許番号
US06284796B1

反応ノート

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