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

HRID 488020

反応式

HRID 488020 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-butoxide2 回

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

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).

後処理

  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)

出典と根拠

ORDレコード
ord-92c9115116db41ddbf5e0dfb1e21d0b2
出典データセット
uspto-grants-1994_03
特許番号
US05298527

関連ノート

読み込み中…