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

HRID 584168

Reaktionsgleichung

Reaktionsgleichung von HRID 584168
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

Komponenten

7

Edukt 4

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

Produkt 1

HCID 5861913(2E)-3-(3-Pyridinyl)-2-propen-1-olAusbeute 22,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9b31fc68bee54b4091abcb4588b77935
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06924278B2

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