Acetic Acid → trans-4-[2-(Dimethylamino)-ethyl]-4-cyclohexene-1,2-diol

HRID 66400

反応式

HRID 66400 の反応式
[CH3:1][N:2]([CH3:11])[CH2:3][CH2:4][C:5]1[CH2:10][CH:9]=CC[CH:6]=1.[C:12]([OH:15])(=O)[CH3:13].II.C(OCC)(=[O:20])C>C([O-])(=O)C.[Ag+]>[CH3:1][N:2]([CH3:11])[CH2:3][CH2:4][C:5]1[CH2:10][C@@H:9]([OH:20])[C@H:12]([OH:15])[CH2:13][CH:6]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 807Iodine2 回HCID 8857Ethyl AcetateHCID 122289201-[2-(Dimethylamino)ethyl]-1,4-cyclohexadiene

生成物 1

HCID 54092690trans-4-[2-(Dimethylamino)-ethyl]-4-cyclohexene-1,2-diol

試薬・触媒・溶媒 1

HCID 11246Silver acetate触媒

実験手順

A solution of 45 g. (0.3 moles) of 1-[2-(dimethylamino)-ethyl]-1,4-cyclohexadiene from Example 3(a) in 1.5 l. of dry glacial acetic acid is treated with 100 g. of silver acetate and 75 g. of iodine. The mixture is stirred until most of the iodine dissolves and is then heated for two hours at 95°. The reaction solution is cooled, filtered and evaporated in vacuo to give an oil. The oil is taken up in ethyl acetate and washed with aqueous sodium bicarbonate solution. The organic phase is dried (MgSO4) and evaporated to an oil. The oil is taken up in ethyl acetate and treated with HCl in isopropanol. The resulting crude solid is removed by filtration and recrystallized from acetonitrile-ether to yield dl-trans-4-[2-(dimethylamino)-ethyl]-4-cyclohexene-1,2-diol, diacetate ester, hydrochloride salt.

後処理

  1. dissolutiondissolves
  2. temperatureis then heated for two hours at 95°
  3. temperatureThe reaction solution is cooled
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give an oil
  7. washwashed with aqueous sodium bicarbonate solution
  8. dry with materialThe organic phase is dried (MgSO4)
  9. customevaporated to an oil
  10. additiontreated with HCl in isopropanol
  11. customThe resulting crude solid is removed by filtration
  12. customrecrystallized from acetonitrile-ether

出典と根拠

ORDレコード
ord-b120cb378f7d474b876bc775b36ea058
出典データセット
uspto-grants-1978_12
特許番号
US04131744

関連ノート

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