Formic Acid → Methyl 4-[3-carboxy-4-(4-cyanophenyl)butyl]benzoate

HRID 1672662ノート

反応式

HRID 1672662 の反応式
C(N(CC)CC)C.C(O)=O.[C:11]([C:13]1[CH:44]=[CH:43][C:16]([CH2:17][C:18]([CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]([O:41][CH3:42])=[O:40])=[CH:35][CH:34]=2)(C(OCC=C)=O)[C:19]([O:21]CC=C)=[O:20])=[CH:15][CH:14]=1)#[N:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:19]([CH:18]([CH2:17][C:16]1[CH:15]=[CH:14][C:13]([C:11]#[N:12])=[CH:44][CH:43]=1)[CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]([O:41][CH3:42])=[O:40])=[CH:35][CH:34]=1)([OH:21])=[O:20]

参加物

7

反応物 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 57831378Diallyl 2-(4-cyanobenzyl)-2-[2-(4-methoxycarbonylphenyl)ethyl]malonate

生成物 1

HCID 57831382Methyl 4-[3-carboxy-4-(4-cyanophenyl)butyl]benzoate収率 89%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
100 °C

実験手順

A solution of 7.47 ml (53.63 mmol) of triethylamine and 1.53 ml (40.63 mmol) of formic acid in 170 ml of dioxane is added to a solution of 7.5 g (16.25 mmol) of diallyl 2-(4-cyanobenzyl)-2-[2-(4-methoxycarbonylphenyl)ethyl]malonate from Example 71A, 0.3 g (1.14 mmol) of triphenylphosphine and 70 mg of palladium acetate in 170 ml of dioxane at room temperature. The reaction mixture is then stirred at 100° C. for 2 hours. After conversion is complete, the reaction solution is cooled and the solvent is removed in vacuo. The residue is then taken up in ethyl acetate and water and acidified with 1 N hydrochloric acid, and the organic phase is separated off. The aqueous phase is extracted three times more with ethyl acetate, and the organic phases are then combined, washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solution is concentrated in vacuo. 5.48 g (89% yield, 90% purity) of a colorless solid are obtained.

後処理

  1. temperaturethe reaction solution is cooled
  2. customthe solvent is removed in vacuo
  3. customthe organic phase is separated off
  4. extractionThe aqueous phase is extracted three times more with ethyl acetate
  5. washwashed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe solution is concentrated in vacuo
  9. custom5.48 g (89% yield, 90% purity) of a colorless solid are obtained

出典と根拠

ORDレコード
ord-fd2025e0fee94054bb9249c6c322b5c6
出典データセット
uspto-grants-2011_08
特許番号
US07998988B2

反応ノート

読み込み中…