Hydrochloric Acid → 1-(Benzo[b]furan-5-yl)-2-(pyridin-3-ylmethoxy)ethanol

HRID 2257577ノート

反応式

HRID 2257577 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.CC(C)([O-])C.[K+].[O:15]1[CH:19]=[CH:18][C:17]2[CH:20]=[C:21]([CH:24]3[CH2:26][O:25]3)[CH:22]=[CH:23][C:16]1=2.Cl>C(OCC)(=O)C.CS(C)=O>[O:15]1[CH:19]=[CH:18][C:17]2[CH:20]=[C:21]([CH:24]([OH:25])[CH2:26][O:8][CH2:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH:22]=[CH:23][C:16]1=2

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 75103-PyridinemethanolHCID 23665647Potassium tert-butoxideHCID 451225992-(Benzo[b]furan-5-yl)oxirane

生成物 1

HCID 544244681-(Benzo[b]furan-5-yl)-2-(pyridin-3-ylmethoxy)ethanol収率 14.2%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

A mixture of 1.6 g of 3-pyridinemethanol, 1.7 g of potassium tert-butoxide and 23 ml of dimethyl sulfoxide was heated to 80° C. Thereto was added 2.4 g of 2-(benzo[b]furan-5-yl)oxirane. The resulting mixture was stirred at 85°-90° C. for 15 minutes. The reaction mixture was added to a mixture of 50 ml of ice water and 50 ml of ethyl acetate. The resulting mixture was adjusted to pH 1 with 6N hydrochloric acid. The aqueous layer was separated and 30 ml of ethyl acetate was added thereto. The resulting mixture was adjusted to pH 9.5 with potassium carbonate. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by column chromatography (eluant:chloroform/ethanol=50/1) to obtain 0.56 g of 1-(benzo[b]furan-5-yl)-2-(pyridin-3-ylmethoxy)ethanol (compound No. 339).

後処理

  1. customThe aqueous layer was separated
  2. addition30 ml of ethyl acetate was added
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by column chromatography (eluant:chloroform/ethanol=50/1)

出典と根拠

ORDレコード
ord-3e0a77755d494243a109a0d39f72f4b9
出典データセット
uspto-grants-1997_08
特許番号
US05658904

反応ノート

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