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

HRID 1913783노트

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HRID 1913783 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매2회

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-96ca885e457644af93d871a16d85e098
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609727B2

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