Methanol → Methyl 5-hydroxybenzofuran-2-carboxylate

반응식

[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([OH:12])=[O:11])=[CH:7][C:6]=2[CH:13]=1.S(=O)(=O)(O)O.[CH3:19]O>>[CH3:19][O:11][C:10]([C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:13][C:6]=2[CH:7]=1)=[O:12]

참가 물질

반응물 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 122089725-Hydroxybenzofuran-2-carboxylic acid

생성물 1

HCID 12208973Methyl 5-hydroxybenzofuran-2-carboxylate수율 83%

실험 절차

To a solution of 5-hydroxy-benzofuran-2-carboxylic acid (4.6 g, 26.0 mmol) in MeOH (100 mL) was added concentrated sulfuric acid (1.2 g, 13.0 mmol) and the resultant solution was heated (reflux, 18 h). The reaction was cooled (rt) and concentrated in vacuo. The resultant residue was purified by silica gel flash column chromatography using MeOH:DCM (10%) to provide the title compound (4.14 g, 83%). MS (ESI): mass calcd for C10H8O4, 192.0; m/z found, 193.1 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.47 (s, 1H), 7.39 (d, J=9.0, 1H), 7.04 (d, J=2.5, 1H), 6.97 (dd, J=9.0, 2.5, 1H), 3.92 (s, 3H).

후처리

temperature(reflux, 18 h)
concentrationconcentrated in vacuo
customThe resultant residue was purified by silica gel flash column chromatography

출처 및 근거

ORD 기록: ord-f48aca3efcba4a49be61d06c12167734
출처 데이터셋: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08399465B2

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