Ethyl 2-bromo-3-(4-methoxyphenyl)-3-oxopropanoate → HCID 59587379、化合物

HRID 389698ノート

反応式

HRID 389698 の反応式
Br[CH:2]([C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[F:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:20]=1[C:21]([O-:23])=[O:22].[Na+]>C(O)C.CCOC(C)=O.O>[F:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:20]=1[C:21]([O:23][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)=[O:9])=[O:22]

参加物

6

反応物 2

HCID 13048360Ethyl 2-bromo-3-(4-methoxyphenyl)-3-oxopropanoateHCID 23698872Sodium 2,6-difluorobenzoate

生成物 1

HCID 59587379HCID 59587379、化合物収率 96.7%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of ethyl 2-bromo-3-(4-methoxyphenyl)-3-oxopropanoate (0.090 g, 0.3 mmol) and sodium 2,6-difluorobenzoate (0.054 g, 0.30 mmol) in ethanol (2 mL) was heated at 120° C. in the microwave for 10 minutes. The reaction mixture was diluted with EtOAc (25 mL) and water (25 mL). The organic phase was washed with water and brine, dried over MgSO4 and the solvent evaporated in vacuo. The residue was purified by silica gel column chromatography using a gradient of 0-40% EtOAc in hexanes to afford 3-ethoxy-1-(4-methoxyphenyl)-1,3-dioxopropan-2-yl 2,6-difluorobenzoate (0.108 g, 0.29 mmol, 96%) as a clear film. 1H NMR (CDCl3) δ 1.27 (3H, t), 3.89 (3H, s), 4.30 (2H, m), 6.47 (1H, s), 6.97 (4H, m), 7.46 (1H, m), 8.06 (2H, d). LCMS (1) Rt: 2.26 min; m/z (ES+) 379.

後処理

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried over MgSO4
  3. customthe solvent evaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-be4053e71b4a4939b2a17ea4c33a982b
出典データセット
uspto-grants-2013_02
特許番号
US08378095B2

反応ノート

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