Water → Allyl (4'-{[3-(allyloxy)-2-formyl-4-(trifluoromethyl)benzyl]oxy}-3'-fluoro-1,1'-biphenyl-4-yl)acetate

HRID 2076604

反応式

HRID 2076604 の反応式
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[CH:8]=[CH2:9].[F:11][C:12]1[CH:13]=[C:14]([C:33]2[CH:38]=[CH:37][C:36]([CH2:39][C:40]([O:42][CH2:43][CH:44]=[CH2:45])=[O:41])=[CH:35][CH:34]=2)[CH:15]=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[C:22]([OH:30])[C:21]=1[CH:31]=[O:32].O>CN(C)C=O>[CH2:7]([O:30][C:22]1[C:21]([CH:31]=[O:32])=[C:20]([CH:25]=[CH:24][C:23]=1[C:26]([F:29])([F:27])[F:28])[CH2:19][O:18][C:17]1[CH:16]=[CH:15][C:14]([C:33]2[CH:34]=[CH:35][C:36]([CH2:39][C:40]([O:42][CH2:43][CH:44]=[CH2:45])=[O:41])=[CH:37][CH:38]=2)=[CH:13][C:12]=1[F:11])[CH:8]=[CH2:9]

参加物

6

反応物 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 86617402Allyl (3'-fluoro-4'-{[2-formyl-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-1,1'-biphenyl-4-yl)acetate

生成物 1

HCID 86617403Allyl (4'-{[3-(allyloxy)-2-formyl-4-(trifluoromethyl)benzyl]oxy}-3'-fluoro-1,1'-biphenyl-4-yl)acetate収率 24%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

Potassium carbonate (148 mg, 1.07 mmol) and allyl bromide (0.091 ml, 1.1 mmol) were successively added to a solution of allyl (3′-fluoro-4′-{[2-formyl-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-1,1′-biphenyl-4-yl)acetate (476 mg, 0.975 mmol) obtained in Example (12-4) in N,N-dimethylformamide (5 ml), and the mixture was stirred at 50° C. for 1.5 hours. After the reaction mixture was poured into water and the mixture was extracted with ethyl acetate, the organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=3/1) to give allyl (4′-{[3-(allyloxy)-2-formyl-4-(trifluoromethyl)benzyl]oxy}-3′-fluoro-1,1′-biphenyl-4-yl)acetate (122 mg, yield: 24%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe organic layer was successively washed with water
  3. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  4. customThe residue obtained
  5. customby removing the solvent under reduced pressure
  6. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=3/1)

出典と根拠

ORDレコード
ord-9f7463a751fd4bfdaf6dfb066f3aacce
出典データセット
uspto-grants-2011_04
特許番号
US07923573B2

関連ノート

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