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

HRID 1926127ノート

反応式

HRID 1926127 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f67e0c5573474a96a6a9e38a940f11f0
出典データセット
uspto-grants-2012_05
特許番号
US08178543B2

反応ノート

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