Potassium Carbonate → Ethyl-4-(2-methoxy-3-methylphenyl)-4-methyl-2-oxopentanoate

HRID 1443264ノート

反応式

HRID 1443264 の反応式
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][C:4]=1[C:10](O)([CH3:12])[CH3:11].[CH2:14]([O:16][C:17](=[O:25])[C:18]([O:20][Si](C)(C)C)=[CH2:19])[CH3:15].[Sn](Cl)(Cl)(Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH2:14]([O:16][C:17](=[O:25])[C:18](=[O:19])[CH2:20][C:10]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([CH3:9])[C:3]=1[O:2][CH3:1])([CH3:12])[CH3:11])[CH3:15]

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 24287Tin tetrachlorideHCID 111168062-Trimethylsilanyloxy-acrylic acid ethyl esterHCID 179891622-(2-Methoxy-3-methylphenyl)propan-2-ol

生成物 1

HCID 17989129Ethyl-4-(2-methoxy-3-methylphenyl)-4-methyl-2-oxopentanoate収率 41.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

71.37 g (395.96 mmol) of 2-(2-methoxy-3-methylphenyl)-propan-2-ol and 149 g (791.92 mmol) of 2-trimethylsilanyloxyacrylic acid ethyl ester are introduced into 1.1 l of dichloromethane. At −78° C., 44.8 ml (379.91 mmol) of tin tetrachloride is added in drops, and the batch is then stirred for three hours at this low temperature. 1.4 l of semiconcentrated potassium carbonate solution is added in drops, and the reaction mixture is thus brought to room temperature. The batch is filtered, and the filtrate is extracted three times with ethyl acetate. The combined organic extracts are washed with brine, dried on sodium sulfate, and the solvent is spun off. The residue is chromatographed several times on silica gel (mobile solvent: ethyl acetate/hexane). The residue is chromatographed several times on silica gel (mobile solvent: ethyl acetate/hexane). 45.81 g (41.6%) of the desired compound is isolated.

後処理

  1. customis thus brought to room temperature
  2. filtrationThe batch is filtered
  3. extractionthe filtrate is extracted three times with ethyl acetate
  4. washThe combined organic extracts are washed with brine
  5. customdried on sodium sulfate
  6. customThe residue is chromatographed several times on silica gel (mobile solvent: ethyl acetate/hexane)
  7. customThe residue is chromatographed several times on silica gel (mobile solvent: ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-10549c8c5312464e8e82fd08779747ef
出典データセット
uspto-grants-2010_02
特許番号
US07659297B2

反応ノート

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