Hydrochloric Acid → Ethyl 5-hydroxybenzofuran-2-carboxylate

HRID 1058574

反応式

HRID 1058574 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 22228632Ethyl 5-hydroxybenzofuran-2-carboxylate収率 77%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-5292b85848ff4c28acefb19b4c2edb28
出典データセット
uspto-grants-2003_02
特許番号
US06518267B1

関連ノート

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