Sodium Hydroxide → Phenol

HRID 611204ノート

反応式

HRID 611204 の反応式
Cl.[O:2]1[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][C:5]=2[CH:4]=[CH:3]1.[OH-].[Na+].O1C2CNCCC=2C=C1.[C:22](=O)([O:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O.N1C=CC=CC=1>[C:35]1([CH2:34][CH2:33][CH2:32][CH2:31][O:30][C:22]([N:8]2[CH2:9][CH2:10][C:5]3[CH:4]=[CH:3][O:2][C:6]=3[CH2:7]2)=[O:23])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[C:24]1([OH:23])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

参加物

8

反応物 4

HCID 14798Sodium HydroxideHCID 9816881Phenyl 4-phenylbutyl CarbonateHCID 154293314,5,6,7-Tetrahydrofuro[2,3-C]pyridineHCID 195999074,5,6,7-Tetrahydrofuro[2,3-c]pyridine hydrochloride

生成物 2

HCID 996PhenolHCID 196002026-(4-Phenylbutoxycarbonyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1049Pyridine溶媒

実験手順

4,5,6,7-Tetrahydrofuro[2,3-c]pyridine hydrochloride 0.280 g (1.754 mmol) was dissolved in water. The solution was alkalified with aqueous sodium hydroxide and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. A solution of the resulting crude 4,5,6,7-tetrahydrofuro[2,3-c]pyridine and 0.71 g (2.6 mmol) of phenyl 4-phenylbutyl carbonate in 10 ml of pyridine was stirred at 100° C. overnight. The solvent was distilled off under reduced pressure; the resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1 to 9/1) to yield 6-(4-phenylbutoxycarbonyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine as a mixture with phenol.

後処理

  1. extractionextracted with dichloromethane 3 times
  2. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1 to 9/1)

出典と根拠

ORDレコード
ord-359843f0692a49a182fc3bbf482bea6d
出典データセット
uspto-grants-1999_12
特許番号
US05998433

反応ノート

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