Ethyl Acetate → 5-Benzyloxy-2-vinyl-4-pyridone

HRID 1609648

반응식

HRID 1609648 반응식
[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH2:11][C:12]([CH2:15]Cl)=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH2:11][C:12]([CH:15]=[CH2:18])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 677480612-Chloromethyl-5-benzyloxy-4-pyridone

생성물 1

HCID 677480895-Benzyloxy-2-vinyl-4-pyridone수율 66.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 5-benzyloxy-2-chloromethyl-4-pyridone (10.0 g) and triphenylphosphine (10.5 g) in N,N-dimethylformamide (50 ml) was stirred for 5 hours at 90°-100° C. The resulting mixture was poured into ethyl acetate (800 ml). The precipitate was collected by filtration, washed with ethyl acetate and dissolved in dichloromethane (500 ml). To the solution were added water (300 ml) and 38% aqueous formaldehyde (100 ml). The mixture was adjusted to pH 10-10.5 with potassium carbonate. After being stirred for 3 hours at 35°-40° C., the organic layer was separated, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The product was isolated by column chromatography on silica gel with ethyl acetate as an eluent to give 5-benzyloxy-2-vinyl-4-pyridone (6.02 g) .

후처리

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with ethyl acetate
  3. dissolutiondissolved in dichloromethane (500 ml)
  4. additionTo the solution were added water (300 ml) and 38% aqueous formaldehyde (100 ml)
  5. customthe organic layer was separated
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe product was isolated by column chromatography on silica gel with ethyl acetate as an eluent

출처 및 근거

ORD 기록
ord-96ace892f8034357828f3c3ef969b89d
출처 데이터셋
uspto-grants-1995_03
특허 번호
US05401734

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