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

HRID 1656705

반응식

HRID 1656705 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
5 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-430c73b53cba4c019b60cda228d80024
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05254717

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