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

HRID 17617

反応式

HRID 17617 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fcdca3eeee61483893e9bc63ac311015
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

関連ノート

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