Triethylamine → 2-Cyclopropanecarbonyl-7-methoxybenzofuran-4-carboxylic Acid

HRID 1108307노트

반응식

HRID 1108307 반응식
Br[C:2]1[C:7]2[CH:8]=[C:9]([C:11]([CH:13]3[CH2:15][CH2:14]3)=[O:12])[O:10][C:6]=2[C:5]([O:16][CH3:17])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[C]=[O:55].[O:56]1[CH2:60]CCC1.O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:13]1([C:11]([C:9]2[O:10][C:6]3[C:7](=[C:2]([C:60]([OH:56])=[O:55])[CH:3]=[CH:4][C:5]=3[O:16][CH3:17])[CH:8]=2)=[O:12])[CH2:15][CH2:14]1

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 18784855(4-Bromo-7-methoxybenzofuran-2-yl)-cyclopropyl-methanoneHCID 21881883Oxolane--water (1/1)HCID 178418416HCID 178418416, 화합물2회

생성물 1

HCID 187848532-Cyclopropanecarbonyl-7-methoxybenzofuran-4-carboxylic Acid

시약·촉매·용매 1

HCID 167845palladium(II) acetate촉매

실험 절차

To a solution of (4-bromo-7-methoxybenzofuran-2-yl)-cyclopropyl-methanone (1.0 g) in tetrahydrofuran/water (40 ml/20 ml) was added palladium acetate (76 mg), 1,3-bis(diphenylphosphino)propane (280 mg) and triethylamine (4.7 ml). The reaction mixture was heated at 90° C. under a 150 psi atmosphere of carbon monoxide for 3 days. The reaction mixture was allowed to cool to room temperature and the carbon monoxide pressure released. The tetrahydrofuran was removed in vacuo and the aqueous residue washed with ethyl acetate (2×75 ml) and acidified to pH3 with 2M hydrochloric acid. The latter was extracted with ethyl acetate (2×200 ml), the organic layer separated, dried over magnesium sulfate, filtered and concentrated in vacuo to afford the title compound as a pale yellow solid (0.76 g).

후처리

  1. customThe tetrahydrofuran was removed in vacuo
  2. washthe aqueous residue washed with ethyl acetate (2×75 ml)
  3. extractionThe latter was extracted with ethyl acetate (2×200 ml)
  4. customthe organic layer separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-766be0f9dea145f88a483f785c3d20a2
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06066657

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