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

HRID 1913783ノート

反応式

HRID 1913783 の反応式
[C:1]([C:3]1[CH:34]=[CH:33][C:6]([CH2:7][C:8]([CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([O:31][CH3:32])=[O:30])=[CH:25][CH:24]=2)(C(OCC=C)=O)[C:9]([O:11]CC=C)=[O:10])=[CH:5][CH:4]=1)#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.C(O)=O>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:9]([CH:8]([CH2:7][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:34][CH:33]=1)[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([O:31][CH3:32])=[O:30])=[CH:25][CH:24]=1)([OH:11])=[O:10]

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

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 7.5 g (16.25 mmol) of diallyl 2-(4-cyanobenzyl)-2-[2-(4-methoxycarbonylphenyl)ethyl]malonate from Example 46A, 0.3 g (1.14 mmol) of triphenylphosphine and 70 mg of palladium acetate in 170 ml of dioxane is mixed at room temperature with 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. The reaction mixture is then stirred at 100° C. for 2 h. After conversion is complete, the reaction solution is cooled and the solvent is removed in vacuo. The residue is 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 subsequently combined, washed with saturated brine and dried over sodium sulphate. After filtration, the solution is evaporated in vacuo. 5.48 g (89% of theory, 90% purity) of a colourless 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 brine
  6. dry with materialdried over sodium sulphate
  7. filtrationAfter filtration
  8. customthe solution is evaporated in vacuo
  9. custom5.48 g (89% of theory, 90% purity) of a colourless solid are obtained

出典と根拠

ORDレコード
ord-96ca885e457644af93d871a16d85e098
出典データセット
uspto-grants-2013_12
特許番号
US08609727B2

反応ノート

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