Allyl Alcohol → 2-Cyclopropyl-7-(1-hydroxymethylvinyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17617

반응식

HRID 17617 반응식
FC(F)(F)S(O[C:7]1[C:15]2[O:14][C:13]([CH:16]3[CH2:18][CH2:17]3)=[N:12][C:11]=2[C:10]([C:19]#[N:20])=[C:9]([CH3:21])[C:8]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=O)=O.C(N(CC)CC)C.[CH2:37]([OH:40])[CH:38]=[CH2:39]>CN(C)C=O.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:16]1([C:13]2[O:14][C:15]3[C:11](=[C:10]([C:19]#[N:20])[C:9]([CH3:21])=[C:8]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:7]=3[C:38]([CH2:37][OH:40])=[CH2:39])[N:12]=2)[CH2:17][CH2:18]1

참가 물질

7

반응물 3

HCID 7858Allyl AlcoholHCID 8471TriethylamineHCID 866308844-Cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl trifluoromethanesulfonate

생성물 1

HCID 685846992-Cyclopropyl-7-(1-hydroxymethylvinyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile수율 32.5%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

4-Cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl trifluoromethanesulfonate (I-323) (760 mg, 1.80 mmol) was dissolved in dimethylformamide (10 ml), then triethylamine (276 μl, 1.98 mmol), allyl alcohol (209 mg, 3.60 mmol), 1,1′-bis(diphenylphosphino)ferrocene (79.8 mg, 0.144 mmol) and palladium(II) acetate (24.2 mg, 0.108 mmol) were added, followed by stirring in an oil bath at 100° C. under argon atmosphere for 16 hours. The reaction liquid was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, washed with water and saturated brine. After drying over anhydrous sodium sulfate, the insoluble matter was separated by filtration, and the residue obtained by concentration was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=1:1, v/v) to obtain the entitled compound (193 mg, 32%) as a colorless oily substance.

후처리

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water and saturated brine
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. customthe insoluble matter was separated by filtration
  7. customthe residue obtained by concentration
  8. customwas purified by silica gel column chromatography (eluent, n-hexane

출처 및 근거

ORD 기록
ord-fcdca3eeee61483893e9bc63ac311015
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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