Hydrochloric Acid → Ethyl 5-hydroxybenzofuran-2-carboxylate

HRID 1058574

반응식

HRID 1058574 반응식
[Cl-].[Al+3].[Cl-].[Cl-].C(S)C.C[O:9][C:10]1[CH:11]=[CH:12][C:13]2[O:17][C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:15][C:14]=2[CH:23]=1.Cl>ClCCl.O>[OH:9][C:10]1[CH:11]=[CH:12][C:13]2[O:17][C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:15][C:14]=2[CH:23]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 5212832-Benzofurancarboxylic acid, 5-methoxy-, ethyl esterHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 22228632Ethyl 5-hydroxybenzofuran-2-carboxylate수율 77%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a mixture of aluminum chloride (6.3 g, 47.7 mmol) and ethanethiol (4.5 g, 72.9 mmol) in dichloromethane (81 mL) at 0° C. was added ethyl 5-methoxybenzofuran-2-carboxylate (3.0 g, 13.6 mmol). After stirring for 16 h at room temperature, the mixture was poured into water, acidified with 3N HCl and extracted with dichloromethane (2x). The organic layers were combined, washed with brine, collected, dried (MgSO4), filtered and concentrated. The residue was purified by column chromatography (silica gel, ethyl acetate/hexane) to yield the title compound as a white solid (2.16 g, 77%). 1H NMR (400 MHz, CDCl3) δ 7.45 (m, 2H), 7.08 (m, 1H), 7.02 (m, 1H), 5.35 (s b, 1H), 4.44 (q, 2H), 1.42 (t, 3H).

후처리

  1. extractionextracted with dichloromethane (2x)
  2. washwashed with brine
  3. customcollected
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (silica gel, ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-5292b85848ff4c28acefb19b4c2edb28
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06518267B1

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