4-Methylmorpholine → (2E)-3-(3-Pyridinyl)-2-propen-1-ol

HRID 584168

반응식

HRID 584168 반응식
ClC(OCC(C)C)=O.[N:9]1[CH:14]=[CH:13][CH:12]=[C:11](/[CH:15]=[CH:16]/[C:17](O)=[O:18])[CH:10]=1.CN1CCOCC1.[BH4-].[Na+]>COCCOC.O>[N:9]1[CH:14]=[CH:13][CH:12]=[C:11](/[CH:15]=[CH:16]/[CH2:17][OH:18])[CH:10]=1

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 776396trans-3-(3-Pyridyl)acrylic acidHCID 4311764Sodium borohydride

생성물 1

HCID 5861913(2E)-3-(3-Pyridinyl)-2-propen-1-ol수율 22.1%

시약·촉매·용매 2

HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매

실험 절차

Isobutyl chloroformate (4.4 ml) was added dropwise to a suspension of (E)-3-(3-pyridyl)acrylic acid (5.0 g) and N-methylmorpholine (4.05 ml) in 1,2-dimethoxyethane (50 ml) under −18° C. After being stirred at the same temperature for 0.5 hour, a solution of sodium borohydride (1.86 g) in water (10 ml) was added to the mixture all at once. The resulting mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate, and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate as eluent. The fractions containing the objective compound were collected and evaporated under reduced pressure to give (E)-3-(3-pyridyl)-2-propen-1-ol (1.0 g) as an oil.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate as eluent
  6. additionThe fractions containing the objective compound
  7. customwere collected
  8. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-9b31fc68bee54b4091abcb4588b77935
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06924278B2

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