Methanol → 1-(2-Hydroxyethoxy)-2-(2-hydroxyethyl)-3-(tert-butyldiphenylsilyloxy)-propane

HRID 55447노트

반응식

HRID 55447 반응식
[O:1]=[O+][O-].[CH2:4]([O:7][CH2:8][CH:9]([CH2:29][CH:30]=C)[CH2:10][O:11][Si:12]([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C=C.N#N.[BH4-].[Na+].[CH3:36][OH:37]>C(OCC)(=O)C.CCCCCC>[OH:37][CH2:36][CH2:4][O:7][CH2:8][CH:9]([CH2:29][CH2:30][OH:1])[CH2:10][O:11][Si:12]([C:25]([CH3:28])([CH3:26])[CH3:27])([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

7

반응물 5

HCID 887MethanolHCID 947NitrogenHCID 24823OzoneHCID 4311764Sodium borohydrideHCID 187904481-(2-Propene-1-oxy)-2-(2-propene-1-yl)-3-(tert-butyldiphenylsilyloxy)-propane

생성물 1

HCID 187904721-(2-Hydroxyethoxy)-2-(2-hydroxyethyl)-3-(tert-butyldiphenylsilyloxy)-propane수율 72%

시약·촉매·용매 1

HCID 21226206Ethyl acetate hexane용매

실험 절차

Ozone was bubbled through a -78° C. methanol (500 mL) solution of diene, 1-(2-propene-1-oxy)-2-(2-propene-1-yl)-3-(tert-butyldiphenylsilyloxy)-propane, (7.41 g, 18.80 mmol). After the disappearance of the starting material (TLC, 25% ethyl acetate/hexane), the reaction mixture was purged with N2 and sodium borohydride (2.13 g, 56.30 mmol) was added. The reaction was warmed to room temperature. After 12 hours, the reaction was concentrated. The white residue was quenched with water, and extracted with ethyl acetate (100 mL×3). The combined organic phase was washed with brine, dried, and concentrated under reduced pressure to give a residue. The residue was eluted through a short silica gel column with ethyl acetate/hexane (10% to 50% ethyl acetate gradient) and evaporation of the eluting solvent gave the 1,7-diol, 1-(2-hydroxyethoxy)-2-(2-hydroxyethyl)-3-(tert-butyldiphenylsilyloxy)-propane (5.48 g, 72% yield). Rf =0.21 (50% ethyl acetate in hexane). NMR.

후처리

  1. additionwas added
  2. concentrationthe reaction was concentrated
  3. customThe white residue was quenched with water
  4. extractionextracted with ethyl acetate (100 mL×3)
  5. washThe combined organic phase was washed with brine
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customto give a residue
  9. washThe residue was eluted through a short silica gel column with ethyl acetate/hexane (10% to 50% ethyl acetate gradient) and evaporation of the eluting solvent

출처 및 근거

ORD 기록
ord-f422a2017eb94ca48da560e4a1f68c7e
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624949

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