Dimethylformamide → Ethyl 2-methyl-3-(4-methylphenyl)-2-propenoate

HRID 29116

反応式

HRID 29116 の反応式
CN(C)C=O.CC(C)([O-])C.[Na+].[CH3:12][CH2:13][O:14][C:15]([CH:17](P(OCC)(OCC)=O)[CH3:18])=[O:16].[CH3:27][C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1>O>[CH3:18][C:17](=[CH:32][C:31]1[CH:34]=[CH:35][C:28]([CH3:27])=[CH:29][CH:30]=1)[C:15]([O:14][CH2:13][CH3:12])=[O:16]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 77254-MethylbenzaldehydeHCID 107155Triethyl 2-phosphonopropionateHCID 23676156Sodium t-butoxide

生成物 1

HCID 68712312Ethyl 2-methyl-3-(4-methylphenyl)-2-propenoate収率 98.8%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
-2.5 °C

実験手順

To dimethylformamide (1802 ml) that had been cooled to −10° C. was added sodium tert-butoxide (528.6 g) and the solution was stirred at −5 to 0° C. for 30 min. Triethyl 2-phosphonopropionate (1310 g) was added dropwise thereto at 10° C. or below. The solution was stirred at 2 to 5° C. for 1 hr, and 4-methylbenzaldehyde (600.8 g) was added dropwise thereto at 10° C. or below and the solution was stirred at room temperature for 1 hr. Water was added thereto and the solution was extracted with toluene. The extract was washed with water and the solvent was distilled off to give the title compound as an oil (1009 g, yield 98.8%).

後処理

  1. customat 10° C. or below
  2. stirringThe solution was stirred at 2 to 5° C. for 1 hr
  3. stirringat 10° C. or below and the solution was stirred at room temperature for 1 hr
  4. extractionthe solution was extracted with toluene
  5. washThe extract was washed with water
  6. distillationthe solvent was distilled off

出典と根拠

ORDレコード
ord-2eb2a4dd9a0740a3b26f8005a0b593f5
出典データセット
uspto-grants-2008_09
特許番号
US07420070B2

関連ノート

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