Methanol → 6-Methoxy-1-benzofuran-2-carboxylic acid

HRID 717706

반응식

HRID 717706 반응식
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]2[CH:7]=[C:8]([C:10]([O:12]CC)=[O:11])[O:9][C:5]=2[CH:4]=1.CO.[Li+].[OH-]>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]2[CH:7]=[C:8]([C:10]([OH:12])=[O:11])[O:9][C:5]=2[CH:4]=1

참가 물질

6

반응물 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 11830962Ethyl 6-methoxybenzofuran-2-carboxylate

생성물 1

HCID 9188636-Methoxy-1-benzofuran-2-carboxylic acid수율 91%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of Product of Step B (0.25 g, 1.21 mmol) in a mixture of THF, MeOH and H2O (5 ml:2 ml:1 ml), LiOH (0.145 g, 6 mmol) in H2O (0.5 ml) was added and the mixture was stirred for 3 h at room temp. The solvents were distilled off and the residue was portioned between EtOAc (20 ml) and 1M HCl (2 ml). The organic layer was washed with H2O, dried over MgSO4 and filtered. The filtrate was evaporated to dryness to give the title compound (0.21 g, 91%), as a colourless solid. 1H-NMR (DMSO-d6) 7.61 (d, 1H, J=8.67 Hz); 7.54 (s, 1H); 7.24 (d, 1H, J=1.59 Hz); 6.93 (dd, 1H, J=8.67, 2.4 Hz); 3.8 (s, 3H).

후처리

  1. additionwas added
  2. distillationThe solvents were distilled off
  3. washThe organic layer was washed with H2O
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness

출처 및 근거

ORD 기록
ord-24371ff142734ca1a8a5b30910cd56a1
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193716B2

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