Sodium Hydroxide → Phenol

HRID 611198노트

반응식

HRID 611198 반응식
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

참가 물질

6

반응물 3

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

생성물 2

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ae59c4f817df407a9dfd67b2e96e6f45
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998433

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