Hydrochloric Acid → 3-[4-(5-Methoxy-2-methyl-phenoxy)-2-methyl-phenyl]-acrylic acid ethyl ester

HRID 1822342

反応式

HRID 1822342 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:10])=[C:7]([OH:9])[CH:8]=1.[CH2:11]([O:13][C:14](=[O:25])[CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][C:20](F)=[CH:19][C:18]=1[CH3:24])[CH3:12].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[CH2:11]([O:13][C:14](=[O:25])[CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][C:20]([O:9][C:7]2[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[CH3:10])=[CH:19][C:18]=1[CH3:24])[CH3:12]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 109535825-Methoxy-2-methylphenolHCID 537177243-(4-Fluoro-2-methyl-phenyl)-acrylic acid ethyl ester

生成物 1

HCID 690715883-[4-(5-Methoxy-2-methyl-phenoxy)-2-methyl-phenyl]-acrylic acid ethyl ester収率 47.2%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
140 °C

実験手順

The compounds of 5-methoxy-2-methyl-phenol (1.46 g, 9.60 mmol), 3-(4-fluoro-2-methyl-phenyl)-acrylic acid ethyl ester (1.00 g, 4.80 mmol), potassium carbonate (1.33 g, 9.60 mmol) are dissolved in dimethylsulfoxide (12 mL) under nitrogen, and the mixture is stirred overnight at 140° C. HCl 10% is added, and the mixture is extracted with diethyl ether. The organic layer is washed with water, dried (Na2SO4) and filtered, and then the solvent is evaporated in vacuo. Purification by flash chromatography by eluting with hexane:ethyl acetate 10:1 to afford the title compound (0.74 g, 47%). Rf=0.44 (hexane:ethyl acetate 5:1). 1H NMR (300 MHz, CDCl3): δ1.34 (t, 3H, J=7.3 Hz), 2.13 (s, 3H), 2.40 (s, 3H), 3.74 (s, 3H), 4.26 (q, 2H, J=7.1 Hz), 6.28 (d, 1H, J=15.9 Hz), 6.53 (d, 1H, J=2.4 Hz), 6.66-6.73 (m, 3H), 7.15 (d, 1H, J=8.3 Hz), 7.51 (d, 1H, J=8.3 Hz), 7.93 (d, 1H, J=16.0 Hz).

後処理

  1. extractionthe mixture is extracted with diethyl ether
  2. washThe organic layer is washed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent is evaporated in vacuo
  6. customPurification by flash chromatography
  7. washby eluting with hexane:ethyl acetate 10:1

出典と根拠

ORDレコード
ord-026c8309746a46508710020b08ba8d96
出典データセット
uspto-grants-2009_10
特許番号
US07608639B2

関連ノート

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