Dimethylformamide → 3-Benzofurancarboxylic acid, methyl ester

HRID 1091311

반응식

HRID 1091311 반응식
CN(C=[O:5])C.[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8]([O:15]S(C(F)(F)F)(=O)=O)=[CH:7]1.C(N([CH2:28][CH3:29])CC)C>C1(P[C-]2C=CC=C2)C=CC=CC=1.[C-]1(PC2C=CC=CC=2)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CO>[CH3:7][O:6][C:10]([C:9]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:28][C:29]=2[O:15][CH:8]=1)=[O:5]

참가 물질

7

반응물 3

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 21480510Benzo[b]furan-3-yl trifluoromethanesulfonate

생성물 1

HCID 127770993-Benzofurancarboxylic acid, methyl ester수율 86%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 133083342Bis(cyclopenta-2,4-dien-1-yl(phenyl)phosphane);iron(2+)촉매HCID 887Methanol용매

반응 조건

온도
60 °C

실험 절차

To a DMF (8.0 mL) solution of 1-benzofuran-3-yl trifluoromethanesulfonic acid (1.00 g, 3.76 mmol), 1,1′-diphenylphosphinoferrocene (128 mg, 231 μmol) and palladium acetate (26.0 mg, 116 μmol), methanol (3.5 mL) and triethylamine (1.05 mL, 7.53 mmol) were added thereto at room temperature. Carbon monoxide gas was bubbled for 20 minutes, and then under a carbon monoxide atmosphere, the mixture was heated and stirred at 60° C. for 3 hours. Water (50 mL) was added, and then the mixture was extracted with ethyl acetate (2×30 mL). The organic layer was combined, washed with 1N-hydrochloric acid (30 mL), and then dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure. The obtained residue was purified using silica gel flash column chromatography (Biotage AB: column No. 40M, hexane:diethyl ether=95:5), to obtain the title compound (570 mg, 3.24 mmol, 86%) as a transparent oily matter.

후처리

  1. customat room temperature
  2. customCarbon monoxide gas was bubbled for 20 minutes
  3. temperatureunder a carbon monoxide atmosphere, the mixture was heated
  4. additionWater (50 mL) was added
  5. extractionthe mixture was extracted with ethyl acetate (2×30 mL)
  6. washwashed with 1N-hydrochloric acid (30 mL)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationThe solvent was concentrated under reduced pressure
  9. customThe obtained residue was purified

출처 및 근거

ORD 기록
ord-4307a233a64144fb982e361feb07303a
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129366B2

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