Dichloromethane → 4-fluoro-3-phenoxybenzyl (RS)-2-(2-methylpyrimidin-5-yl)-3,3-dimethylbutanoate

HRID 1088312노트

반응식

HRID 1088312 반응식
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12]Br)=[CH:10][C:9]=1[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:23][C:24]1[N:29]=[CH:28][C:27]([CH:30]([C:34]([CH3:37])([CH3:36])[CH3:35])[C:31]([OH:33])=[O:32])=[CH:26][N:25]=1.ClCCl>CC(C)=O.C(OCC)(=O)C>[CH3:23][C:24]1[N:29]=[CH:28][C:27]([CH:30]([C:34]([CH3:37])([CH3:36])[CH3:35])[C:31]([O:33][CH2:12][C:11]2[CH:14]=[CH:15][C:8]([F:7])=[C:9]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:10]=2)=[O:32])=[CH:26][N:25]=1

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 129227144-(Bromomethyl)-1-fluoro-2-phenoxybenzeneHCID 14718723(RS)-2-(2-methylpyrimidin-5-yl)-3,3-dimethylbutanoic acid

생성물 1

HCID 147188194-fluoro-3-phenoxybenzyl (RS)-2-(2-methylpyrimidin-5-yl)-3,3-dimethylbutanoate수율 56.8%

시약·촉매·용매 2

HCID 180Acetone용매HCID 8857Ethyl Acetate용매

실험 절차

Solid potassium carbonate (0.4 g) was added to a solution of 4-fluoro-3-phenoxybenzyl bromide (0.4 g) and (RS)-2-(2-methylpyrimidin-5-yl)-3,3-dimethylbutanoic acid (0.3 g) in acetone (20 cm3), and the mixture was stirred for a period of 6 hours. After standing for a further 2 days, the reaction mixture was filtered, the residue washed with acetone, and the combined filtrate and acetone washings concentrated by evaporation of the solvent under reduced pressure to give an orange oil. Column chromatography on silica gel using dichloromethane followed by ethyl acetate as eluent gave 4-fluoro-3-phenoxybenzyl (RS)-2-(2-methylpyrimidin-5-yl)-3,3-dimethylbutanoate (0.33 g) as an orange oil, which solidified on standing.

후처리

  1. waitAfter standing for a further 2 days
  2. filtrationthe reaction mixture was filtered
  3. washthe residue washed with acetone
  4. concentrationthe combined filtrate and acetone washings concentrated by evaporation of the solvent under reduced pressure
  5. customto give an orange oil

출처 및 근거

ORD 기록
ord-9c09588639b8415ba540900dbe06c818
출처 데이터셋
uspto-grants-1990_10
특허 번호
US04962109

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