Lithium Chloride → 5-Methoxy-2-methyl-benzofuran-7-carboxylic acid methyl ester

HRID 1643543

反応式

HRID 1643543 の反応式
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6]([CH2:12][CH:13]=[CH2:14])[C:5]=1[OH:15].[Li+].[Cl-]>CN(C=O)C.O.CC([O-])=O.CC([O-])=O.[Cu+2].Cl[Pd]Cl>[CH3:1][O:2][C:3]([C:4]1[C:5]2[O:15][C:13]([CH3:14])=[CH:12][C:6]=2[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)=[O:16]

参加物

7

反応物 2

HCID 433294Lithium ChlorideHCID 14838669HCID 14838669、化合物

生成物 1

HCID 595604655-Methoxy-2-methyl-benzofuran-7-carboxylic acid methyl ester収率 100.9%

試薬・触媒・溶媒 4

HCID 8895Cupric acetate触媒HCID 24290Palladium Chloride触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-allyl-2-hydroxy-5-methoxy-benzoic acid methyl ester (4b) (1.48 g, 6.66 mmol) in DMF (30 mL) was added Cu(OAc)2 (3.63 g, 19.98 mmol), LiCl (847 mg, 19.98 mmol) in H2O (1 mL) and PdCl2 (24 mg, 0.133 mmol). The reaction mixture was stirred at RT for 3 h, quenched with H2O (100 mL) and NH4OH (5 mL) and extracted with EtOAc (100 mL). The organic layer was washed with H2O (100 mL), dried over MgSO4 and concentrated. The residue was purified by flash column chromatograph eluting with 10-15% EtOAc/hexane to give colorless oil (1.48 g, 48%). 1H NMR (400 MHz, CDCl3) δ 7.43 (d, J=2.53 Hz, 1 H) 7.17 (d, J=2.53 Hz, 1 H) 6.36 (s, 1 H) 4.00 (s, 3 H) 3.87 (s, 3 H) 2.51 (s, 3 H)

後処理

  1. customquenched with H2O (100 mL) and NH4OH (5 mL)
  2. extractionextracted with EtOAc (100 mL)
  3. washThe organic layer was washed with H2O (100 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatograph
  7. washeluting with 10-15% EtOAc/hexane

出典と根拠

ORDレコード
ord-acc340d7a3a844cf94629aad272434ef
出典データセット
uspto-grants-2012_02
特許番号
US08119624B2

関連ノート

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