Diethyl Ether → 5,9,13-Trimethyltetradeca-4,6-dien-3-one

HRID 1576590ノート

反応式

HRID 1576590 の反応式
[CH3:1][C:2](/[CH:7]=[CH:8]\[CH2:9][CH:10]([CH3:17])[CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:3][C:4]([OH:6])=O.[CH3:18][CH2:19]OCC.C([Li])C.[Cl-].[NH4+]>C1C=CC=CC=1>[CH3:1][C:2]([CH:7]=[CH:8][CH2:9][CH:10]([CH3:17])[CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:3][C:4](=[O:6])[CH2:18][CH3:19]

参加物

6

反応物 4

HCID 3283Diethyl Ether2 回HCID 25517Ammonium ChlorideHCID 86734009cis 3,7,11-Trimethyldodeca-2,4-dienoic acidHCID 178506846HCID 178506846、化合物

生成物 1

HCID 538819695,9,13-Trimethyltetradeca-4,6-dien-3-one

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

To a solution of 3.00 g. of trans/cis 3,7,11-trimethyldodeca-2,4-dienoic acid in 50 ml. ether at 0° under nitrogen is added 28.00 ml. of 0.9 M solution of ethyllithium in benzene. The solution is stirred for 1/2 hour at 0° and then overnight at room temperature. To the reaction mixture is added 50 ml. of ether and the resultant solution is added dropwise with stirring to 300 ml. saturated aqueous ammonium chloride. The organic layer is separated and is washed in turn with 50 ml. saturated aqueous ammonium chloride, 35 ml. water, and 35 ml. saturated aqueous sodium chloride. The solution is dried over calcium sulfate, is concentrated and is then purified by preparative thin layer chromatography (1:3 ether/hexane) and short path distillation (boiling point 100° at .18 mm.) to give 5,9,13-trimethyltetradeca-4,6-dien-3-one (85.4% trans-4, trans-6; 14.6% cis-4, trans-6.).

後処理

  1. customovernight
  2. customat room temperature
  3. additionTo the reaction mixture is added 50 ml
  4. stirringwith stirring to 300 ml
  5. customThe organic layer is separated
  6. washis washed in turn with 50 ml
  7. dry with materialThe solution is dried over calcium sulfate
  8. concentrationis concentrated
  9. distillationis then purified by preparative thin layer chromatography (1:3 ether/hexane) and short path distillation (boiling point 100° at .18 mm.)

出典と根拠

ORDレコード
ord-c0dbd2de10f84df3b9c805a76364ba11
出典データセット
uspto-grants-1976_09
特許番号
US03981922

反応ノート

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