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

HRID 400234

반응식

HRID 400234 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 180Acetone용매HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ede2c44152fa49799c2be5af1e02fafb
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05827868

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