Acetic Acid → alpha-Methyl-2-pyridineethanol

HRID 1974122ノート

反応式

HRID 1974122 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17].C(O)(=O)C>C1C=CC=CC=1>[N:11]1[CH:6]=[CH:7][CH:2]=[CH:3][C:4]=1[CH2:5][CH:8]([OH:10])[CH3:9].[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:9])=[CH:17][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][N:11]=2)=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 176Acetic AcidHCID 7466p-BromoacetophenoneHCID 79752-Methylpyridine

生成物 2

HCID 578865alpha-Methyl-2-pyridineethanol収率 63%HCID 541806622-[2-(4-Bromophenyl)prop-1-en-1-yl]pyridine収率 26%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

2-p-Bromophenyl)- 1-(2-pyridyl-2-propanol is prepared from p-bromoacetophenone and 2-picoline according to the method of Villani, et al., J. Med. Chem., 13, 359 (1970) in 63% yield. This alcohol (129.1 g.) is dehydrated by heating in 1150 ml. of acetic acid-12N hydrochloric acid (3:1) at reflux temperature for 4 hr. The mixture is evaporated in vacuo, made basic with concetrated ammonium hydroxide, and extracted with ethyl acetate. The ethyl acetate extract is washed with water and brine, dried over sodium sulfate, and evaporated to give a dark brown oil. A solution of the oil in benzene is passed through a columm of silica gel. Evaporation of the eluate gave 46.4 g. (26% yield) of crystalline 2-(p-bromophenyl)-1-(2-pyridyl)propene, m.p. 71.5°-73.5° C. (corr.).

後処理

  1. temperatureby heating in 1150 ml
  2. customThe mixture is evaporated in vacuo
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washis washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customto give a dark brown oil
  9. customEvaporation of the eluate
  10. customgave 46.4 g

出典と根拠

ORDレコード
ord-628154c6133143d3b18e28a29e986258
出典データセット
uspto-grants-1976_12
特許番号
US04000143

反応ノート

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