Dimethylformamide → Methyl 2-phenylbenzofuran-5-carboxylate

HRID 2120588ノート

反応式

HRID 2120588 の反応式
I[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[C:13]1([C:19]#[CH:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CN(C)C(=N)N(C)C.CN(C=O)C>[Cu]I.O>[CH3:8][O:7][C:5]([C:4]1[CH:9]=[CH:10][C:11]2[O:12][C:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:20][C:2]=2[CH:3]=1)=[O:6]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 10821PhenylacetyleneHCID 664601,1,3,3-TetramethylguanidineHCID 11346465Methyl 4-hydroxy-3-iodobenzoate

生成物 1

HCID 66865443Methyl 2-phenylbenzofuran-5-carboxylate収率 99.1%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒

実験手順

A mixture of methyl 3-iodo-4-hydroxybenzoate 26 (1 g, 3.6 mmol), phenylacetylene (2 ml, 18 mmol), tetramethylguanidine (4.5 ml, 36 mmol), copper(I)iodide (34 mg, 1.8 mmol), bis(triphenylphosphine)palladium (II)chloride (130 mg, 1.8 mmol) and DMF (20 ml) was stirred at room temperature overnight. The reaction mixture was poured into water, extracted, washed and dried. After evaporation of the solvent, the residue was purified by chromatography to give about 0.9 g of 2-phenyl-benzofuran-5-carboxylic acid methyl ester 27.

後処理

  1. extractionextracted
  2. washwashed
  3. customdried
  4. customAfter evaporation of the solvent
  5. customthe residue was purified by chromatography

出典と根拠

ORDレコード
ord-53d73c4db76444b18bb7af91de18f0dc
出典データセット
uspto-grants-2004_02
特許番号
US06693098B2

反応ノート

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