Sodium Hydroxide → Phenol

HRID 611204노트

반응식

HRID 611204 반응식
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

참가 물질

8

반응물 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

생성물 2

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

시약·촉매·용매 2

HCID 962Water용매HCID 1049Pyridine용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-359843f0692a49a182fc3bbf482bea6d
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998433

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