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

HRID 488020

반응식

HRID 488020 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-butoxide2회

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

At 5° C. 11.2 g (0.1 mol) of potassium tert-butanolate was added to a A mixture of 37.1 g (100 mmol) of ethyltriphenylphosphonium bromide was added under a nitrogen blanket to 300 ml of absolute tetrahydrofuran. At 5° C., 11.2 g (0.1 mol) of potassium tert-butanolate was added. After the mixture had been stirred for 1 hour at 5° C., 20.8 g (100 mmol) of methyl 2-methoxymethylphenylglyoxylate in 100 ml of tetrahydrofuran was dripped in. The mixture wa stirred for 1 hour at 5° C. and for 1 hour at 25° C., 200 ml of water was added and extraction carried out with methylene chloride. After the combined organic phases had been washed with water and dried, the solvent was removed under reduced pressure. The residue was purified chromatographically in a silica gel column (methyl tert-butyl ether/n-hexane=1/2). There was obtained 17.2 g (78%) of the above-mentioned ester as an oil (Z/E isomer=1/9) (compound no. 25).

후처리

  1. customAt 5° C
  2. stirringThe mixture wa stirred for 1 hour at 5° C. and for 1 hour at 25° C.
  3. extractionextraction
  4. washAfter the combined organic phases had been washed with water
  5. customdried
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified chromatographically in a silica gel column (methyl tert-butyl ether/n-hexane=1/2)

출처 및 근거

ORD 기록
ord-92c9115116db41ddbf5e0dfb1e21d0b2
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05298527

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