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

HRID 1108307ノート

反応式

HRID 1108307 の反応式
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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 167845palladium(II) acetate触媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-766be0f9dea145f88a483f785c3d20a2
出典データセット
uspto-grants-2000_05
特許番号
US06066657

反応ノート

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