Hydrochloric Acid → alpha-[4-(Benzyloxy)-3-methoxyphenyl]-3-pyridinemethanol

HRID 274432노트

반응식

HRID 274432 반응식
C([Li])(C)(C)C.[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17](Br)=[CH:16][C:15]=1[O:21][CH3:22])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]=[O:30])[CH:24]=1.Cl>O1CCCC1>[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([CH:29]([C:25]2[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=2)[OH:30])=[CH:16][C:15]=1[O:21][CH3:22])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 103713-PyridinecarboxaldehydeHCID 36131281-(Benzyloxy)-4-bromo-2-methoxybenzeneHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 13365804alpha-[4-(Benzyloxy)-3-methoxyphenyl]-3-pyridinemethanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

aa) 10 ml of tert.butyl lithium solution (1.4M in hexane) are added dropwise at -70° within 10 minutes to 4.1 g of 4-(benzyloxy)-3-methoxy-bromobenzene dissolved in 40 ml of tetrahydrofuran. After stirring at -70° for 2 hours. 1 ml of pyridine-3-carbaldehyde is added within 5 minutes. The reaction mixture is stirred at -70° for 1 hour and at 0° for 2 hours, and poured into 100 ml of 1N hydrochloric acid. The mixture is extracted three times with 50 ml of ether each time. The combined ether phases are washed with 100 ml of 1N hydrochloric acid and 20 ml of water. The combined aqueous phases are made alkaline with aqueous ammonia solution and extracted three times with 100 ml of methylene chloride each time. The combined methylene chloride phases are dried over sodium sulfate and evaporated. There is obtained alpha-[4-(benzyloxy)-3 -methoxyphenyl]-3-pyridinemethanol as an oil.

후처리

  1. stirringThe reaction mixture is stirred at -70° for 1 hour and at 0° for 2 hours
  2. extractionThe mixture is extracted three times with 50 ml of ether each time
  3. washThe combined ether phases are washed with 100 ml of 1N hydrochloric acid and 20 ml of water
  4. extractionextracted three times with 100 ml of methylene chloride each time
  5. dry with materialThe combined methylene chloride phases are dried over sodium sulfate
  6. customevaporated

출처 및 근거

ORD 기록
ord-d5228a64ac4745ecb47e1a28a26920ee
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05389653

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