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

HRID 1576590노트

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HRID 1576590 반응식
[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]

참가 물질

6

반응물 4

HCID 3283Diethyl Ether2회HCID 25517Ammonium ChlorideHCID 86734009cis 3,7,11-Trimethyldodeca-2,4-dienoic acidHCID 178506846HCID 178506846, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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.).

후처리

  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.)

출처 및 근거

ORD 기록
ord-c0dbd2de10f84df3b9c805a76364ba11
출처 데이터셋
uspto-grants-1976_09
특허 번호
US03981922

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