Water → 4-{[Tert-butyl(dimethyl)silyl]oxy}but-2-yn-1-yl methanesulfonate

HRID 1926127노트

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HRID 1926127 반응식
[Si:1]([O:8][CH2:9][C:10]#[C:11][CH2:12][OH:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].O>C(OCC)(=O)C>[CH3:21][S:22]([O:13][CH2:12][C:11]#[C:10][CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])(=[O:24])=[O:23]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54618454-((Tert-butyldimethylsilyl)oxy)but-2-yn-1-ol

생성물 1

HCID 866157794-{[Tert-butyl(dimethyl)silyl]oxy}but-2-yn-1-yl methanesulfonate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

4-{[Tert-butyl(dimethyl)silyl]oxy}but-2-yn-1-ol (701.4 mg) was dissolved in ethyl acetate (15 mL), and the solution was cooled to 0° C. Triethylamine (1.1 mL) and methanesulfonyl chloride (0.3 mL) were added, and the mixture was stirred at 0° C. for 3 hrs. Water was added to the reaction mixture and the mixture was extracted with diethyl ether. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=90:10→50:50) to give the title compound (469.7 mg) as a colorless oil.

후처리

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified by silica gel column chromatography (eluent, hexane:ethyl acetate=90:10→50:50)

출처 및 근거

ORD 기록
ord-f67e0c5573474a96a6a9e38a940f11f0
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178543B2

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