Diethyl methylmalonate → (+/-)-2-(2-(2-Naphthyl)benzyl)propionic acid

HRID 356837ノート

反応式

HRID 356837 の反応式
[CH3:1][CH:2]([C:8](OCC)=O)[C:3]([O:5]CC)=[O:4].[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1CBr>O.[Na]>[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:8][CH:2]([CH3:1])[C:3]([OH:5])=[O:4]

参加物

5

反応物 2

HCID 11857Diethyl methylmalonateHCID 226765282-[2-(Bromomethyl)phenyl]naphthalene

生成物 1

HCID 22676534(+/-)-2-(2-(2-Naphthyl)benzyl)propionic acid収率 83,774.203%

試薬・触媒・溶媒 2

HCID 5360545Sodium触媒HCID 962Water溶媒4 回

反応条件

温度
130 °C

実験手順

70 g (0.37 mmol) of diethyl methylmalonate dissolved in 50 cm3 of H2O-free EtOH were added dropwise at room temperature to 8.5 g (0.37 mmol) of sodium in 100 cm3 of H2O-free EtOH. 110 g (0.37 mmol) of 26 in 200 cm3 of H2O-free EtOH were subsequently added dropwise, and the mixture was refluxed for 3 hours. 62 g (1.1 mol) of KOB dissolved in 100 cm3 of H2O were added at room temperature, and the mixture was refluxed for a further 4 hours. The solvent was removed in vacuo, H2O was added to the residue until the latter had dissolved completely, and the mixture was acidified to pH 1 by means of concentrated aqueous HCl. The precipitate which had formed was filtered off with suction, dried and heated at 130° C. for 1 hour, giving 90 g (84%) of 27 as a viscous oil.

後処理

  1. temperaturethe mixture was refluxed for 3 hours
  2. additionwere added at room temperature
  3. temperaturethe mixture was refluxed for a further 4 hours
  4. customThe solvent was removed in vacuo, H2O
  5. additionwas added to the residue until the latter
  6. dissolutionhad dissolved completely
  7. customThe precipitate which had formed
  8. filtrationwas filtered off with suction
  9. customdried

出典と根拠

ORDレコード
ord-83a173e412c047fb87c7286b7145c66d
出典データセット
uspto-grants-1998_11
特許番号
US05840644

反応ノート

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