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

HRID 1177070

반응식

HRID 1177070 반응식
[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]

참가 물질

7

반응물 2

HCID 433294Lithium ChlorideHCID 14838669HCID 14838669, 화합물

생성물 1

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

시약·촉매·용매 4

HCID 8895Cupric acetate촉매HCID 24290Palladium Chloride촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-f18dbbf2800d41dcb6a3952f62647bed
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842713B2

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