Methyl vinyl ketone → (3E)-4-[6-(benzyloxy)pyridin-3-yl]but-3-en-2-one

HRID 384479노트

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HRID 384479 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][C:17](=[O:20])[CH:18]=[CH2:19].C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C=O)C.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[N:10]=[CH:11][C:12](/[CH:19]=[CH:18]/[C:17](=[O:20])[CH3:16])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 6570Methyl vinyl ketoneHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 111081912-Benzyloxy-5-bromopyridine

생성물 1

HCID 59527049(3E)-4-[6-(benzyloxy)pyridin-3-yl]but-3-en-2-one수율 38.2%

시약·촉매·용매 2

HCID 9832798Tris(dibenzylideneacetone) dipalladium촉매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

To a solution of 2-(benzyloxy)-5-bromopyridine (600 mg) in DMF (12 mL) were added 3-buten-2-one (400 mg), tris(dibenzylidene acetone) dipalladium(0) (74 mg), triethylamine (460 mg), and tris(o-tolyl)phosphine (70 mg) at room temperature under nitrogen flow, and the mixture was stirred at 100° C. for 24 hours. The reaction liquid was allowed to cool, and insolubles were filtered through Celite. Water was added to the filtrate, followed by three times extractions with ethyl acetate. The organic layer was washed sequentially with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1-3/2) to obtain (3E)-4-[6-(benzyloxy)pyridin-3-yl]but-3-en-2-one (220 mg).

후처리

  1. customThe reaction liquid
  2. temperatureto cool
  3. filtrationinsolubles were filtered through Celite
  4. additionWater was added to the filtrate
  5. extractionfollowed by three times extractions with ethyl acetate
  6. washThe organic layer was washed sequentially with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9/1-3/2)

출처 및 근거

ORD 기록
ord-a7d9c3a42b1e4405a47656ffc0a80660
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367702B2

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