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

HRID 1672662노트

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HRID 1672662 반응식
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]

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]benzoate수율 89%

시약·촉매·용매 2

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

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온도
100 °C

실험 절차

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.

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 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

출처 및 근거

ORD 기록
ord-fd2025e0fee94054bb9249c6c322b5c6
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998988B2

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