Sodium Hydroxide → Phenol

HRID 611198ノート

反応式

HRID 611198 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.[C:11](=O)([O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>N1C=CC=CC=1>[C:24]1([CH2:23][CH2:22][CH2:21][CH2:20][O:19][C:11]([N:8]2[CH2:9][CH2:10][C:5]3[CH:4]=[CH:3][O:2][C:6]=3[CH2:7]2)=[O:12])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[C:13]1([OH:12])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 9816881Phenyl 4-phenylbutyl CarbonateHCID 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 1

HCID 1049Pyridine溶媒

実験手順

A solution of 0.226 g (1.416 mmol) of 4,5,6,7-tetrahydrofuro[2,3-c]pyridine hydrochloride and 0.57 g (2.1 mmol) of phenyl 4-phenylbutyl carbonate in 10 ml of pyridine was stirred at 100° C. overnight. The reaction mixture was poured into aqueous sodium hydroxide and extracted with ethyl acetate 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; 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 ethyl acetate 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. 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-ae59c4f817df407a9dfd67b2e96e6f45
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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