p-Toluenesulfonic acid → Oxiranemethanol, 3-[(phenylmethoxy)methyl]-

HRID 400234

反応式

HRID 400234 の反応式
C[O:2]C(OC)(C)C.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11](S(O)(=O)=O)=[CH:10][CH:9]=1.[O:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>CC(C)=O.CCOCC>[CH2:18]([O:19][CH2:24][CH:23]1[O:22][CH:21]1[CH2:20][OH:2])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

6

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 312751,4-Dioxane

生成物 1

HCID 3934498Oxiranemethanol, 3-[(phenylmethoxy)methyl]-

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 3283Diethyl Ether溶媒

実験手順

2,2-Dimethoxypropane (12 mL, 97 mmol) was added with stirring to a solution of crude diols A and B, catalytic p-toluenesulfonic acid in acetone (50 mL). The mixture was stirred at room temperature overnight, diluted with ether and washed with aqueous sodium bicarbonate solution (twice). The organic extract was dried (magnesium sulfate), filtered and concentrated. The crude oil was chromatographed on a silica gel column and eluted with 2-10% ethyl acetate in hexanes to obtain dioxane C (5.85 g, 65% overall yield from 4-benzyloxy-2,3-epoxy-1-butanol) as a colorless oil.

後処理

  1. washwashed with aqueous sodium bicarbonate solution (twice)
  2. extractionThe organic extract
  3. dry with materialwas dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude oil was chromatographed on a silica gel column
  7. washeluted with 2-10% ethyl acetate in hexanes
  8. customto obtain

出典と根拠

ORDレコード
ord-ede2c44152fa49799c2be5af1e02fafb
出典データセット
uspto-grants-1998_10
特許番号
US05827868

関連ノート

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