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

HRID 274432ノート

反応式

HRID 274432 の反応式
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

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 103713-PyridinecarboxaldehydeHCID 36131281-(Benzyloxy)-4-bromo-2-methoxybenzeneHCID 178418306HCID 178418306、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d5228a64ac4745ecb47e1a28a26920ee
出典データセット
uspto-grants-1995_02
特許番号
US05389653

反応ノート

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