Ethylene Oxide → 3-Benzenesulfonyl-3-methyl-butan-1-ol

HRID 2212069ノート

反応式

HRID 2212069 の反応式
C([Li])CCC.[C:6]1([S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:18]1[O:20][CH2:19]1>O1CCCC1>[C:6]1([S:12]([C:15]([CH3:17])([CH3:16])[CH2:19][CH2:18][OH:20])(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

5

反応物 3

HCID 6354Ethylene OxideHCID 199476((1-Methylethyl)sulfonyl)benzeneHCID 178418339Butyllithium

生成物 1

HCID 149069793-Benzenesulfonyl-3-methyl-butan-1-ol収率 99%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-40 °C

実験手順

A solution of n-butyllithium in cyclohexanes (1.8M, 35.1 ml; 63.18 mmol) was added dropwise to a stirred solution of isopropyl phenyl sulphone (9.95 g, 54 mmol) in tetrahydrofuran (100 ml) keeping the temperature of the mixture below −60° C. The mixture was stirred for 30 min. and ethylene oxide was passed through the reaction mixture for 10 min. The mixture was warmed up to −40° C. for 30 min., then quenched with sat. aqueous NH4Cl and extracted into ethyl acetate. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified on silica gel (i-hexane:ethyl acetate) to give the title compound (12.3 g, 99%).

後処理

  1. customthe temperature of the mixture below −60° C
  2. customquenched with sat. aqueous NH4Cl
  3. extractionextracted into ethyl acetate
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel (i-hexane:ethyl acetate)

出典と根拠

ORDレコード
ord-f8737e092ee344178f600929b7151bbd
出典データセット
uspto-grants-2006_09
特許番号
US07101892B2

反応ノート

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