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

HRID 1088312ノート

反応式

HRID 1088312 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9c09588639b8415ba540900dbe06c818
出典データセット
uspto-grants-1990_10
特許番号
US04962109

反応ノート

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