Water → Methyl alpha-(2-methoxymethylphenyl)-beta-methylacrylate

HRID 1656705

反応式

HRID 1656705 の反応式
[C:1]([O-])(C)(C)[CH3:2].[K+].[CH3:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16](=O)[C:17]([O:19][CH3:20])=[O:18].O>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.O1CCCC1>[CH3:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16](=[CH:1][CH3:2])[C:17]([O:19][CH3:20])=[O:18]

参加物

6

反応物 3

HCID 962WaterHCID 19937173Methyl 2-methoxymethylphenylglyoxylateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 54268689Methyl alpha-(2-methoxymethylphenyl)-beta-methylacrylate収率 78.1%

試薬・触媒・溶媒 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
5 °C

実験手順

37.1 g (100 mmol) of ethyltriphenylphosphonium bromide are introduced under nitrogen into 300 ml of absolute tetrahydrofuran. At 5° C., 11.2 g (0.1 mol) of potassium t-butanolate are added. After stirring at 5° C. for one hour, 20.8 g (100 mmol) of methyl 2-methoxymethylphenylglyoxylate in 100 ml of tetrahydrofuran are added dropwise. The mixture is stirred at 5° C. for one hour and at 25° C. for one hour, 200 ml of water are added, the mixture is extracted with methylene chloride and the organic phases are washed with water. After drying over sodium sulfate, the solvent is removed under reduced pressure. The residue is purified by chromatography on a silica gel column (methyl tert-butyl ether/n-hexane=1/2). 17.2 g (78%) of the abovementioned ester are obtained as an oil (Z/E isomer=1/9).

後処理

  1. stirringThe mixture is stirred at 5° C. for one hour and at 25° C. for one hour
  2. extractionthe mixture is extracted with methylene chloride
  3. washthe organic phases are washed with water
  4. dry with materialAfter drying over sodium sulfate
  5. customthe solvent is removed under reduced pressure
  6. customThe residue is purified by chromatography on a silica gel column (methyl tert-butyl ether/n-hexane=1/2)

出典と根拠

ORDレコード
ord-430c73b53cba4c019b60cda228d80024
出典データセット
uspto-grants-1993_10
特許番号
US05254717

関連ノート

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