Formic Acid → Methyl 4-[2-carboxy-4-(4-cyanophenyl)butyl]benzoate

HRID 1927391노트

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HRID 1927391 반응식
C(N(CC)CC)C.C(O)=O.[C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]([O:43][CH3:44])=[O:42])=[CH:37][CH:36]=2)(C(OCC=C)=O)[C:22]([O:24]CC=C)=[O:23])=[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:22]([CH:21]([CH2:20][CH2:19][C:16]1[CH:15]=[CH:14][C:13]([C:11]#[N:12])=[CH:18][CH:17]=1)[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]([O:43][CH3:44])=[O:42])=[CH:37][CH:36]=1)([OH:24])=[O:23]

참가 물질

7

반응물 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 57831389HCID 57831389, 화합물

생성물 1

HCID 57831396Methyl 4-[2-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 41.8 ml (0.3 mol) of triethylamine and 8.6 ml (0.23 mol) of formic acid in 500 ml of dioxane is added to a solution of 43.5 g (0.09 mol) of diallyl 2-[2-(4-cyanophenyl)ethyl]-2-(4-methoxycarbonylbenzyl)malonate, 1.67 g (0.01 mol) of triphenylphosphine and 410 mg of palladium acetate in 505 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 resulting residue is purified by flash chromatography on silica gel (mobile phase: dichloromethane/methanol 50:1). 25 g (74 mmol, 82% of theory) of a colorless solid are obtained.

후처리

  1. temperaturethe reaction solution is cooled
  2. customthe solvent is removed in vacuo
  3. customThe resulting residue is purified by flash chromatography on silica gel (mobile phase: dichloromethane/methanol 50:1)
  4. custom25 g (74 mmol, 82% of theory) of a colorless solid are obtained

출처 및 근거

ORD 기록
ord-f616cffcc6604c6bb69245872c11acc8
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183271B2

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