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

HRID 2076604

반응식

HRID 2076604 반응식
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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-9f7463a751fd4bfdaf6dfb066f3aacce
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07923573B2

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