Water → 2-(1-Methylethyl)-5,9-dimethyl-2,4,8-decatrienal

HRID 5664노트

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HRID 5664 반응식
[CH3:1][CH:2]([C:4](=[CH:7][CH:8]=[C:9]([CH3:16])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[C:5]#N)[CH3:3].[H-].C([Al+]CC(C)C)C(C)C.[OH2:27]>CCCCCC.C1(C)C=CC=CC=1>[CH3:1][CH:2]([C:4](=[CH:7][CH:8]=[C:9]([CH3:16])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH:5]=[O:27])[CH3:3]

참가 물질

6

반응물 3

HCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 540705132-(1-Methylethyl)-5,9-dimethyl-2,4,8-decatrienenitrile

생성물 1

HCID 540485332-(1-Methylethyl)-5,9-dimethyl-2,4,8-decatrienal수율 90%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8058Hexane용매

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온도
-70 °C

실험 절차

To a solution of 2-(1-methylethyl)-5,9-dimethyl-2,4,8-decatrienenitril (2Z compound, 217 mg, 1 mmol) in n-hexane (4 ml) was added a 1 M solution of diisobutylaluminium hydride in toluene (2 ml) with stirring under argon atmosphere at -70° C. After two-hour-stirring at the same temperature, water (0.8 ml) was added to the mixture followed by removal of the cooling bath and vigorous stirring. The resultant while precipitates were filtered and washed with n-hexane. The filtrate was combined with a 10% aqueous solution of oxalic acid and stirred for 3 hours. The organic layer was extracted and separated, washed with water, dried over MgSO4, and concentrated. The above manipulation was conducted under argon atmosphere. The resultant residue was subjected to silica gel column chromatography (solvent: n-hexane/ethyl acetate=50:1) to obtain the aimed 2-(1-methylethyl)-5,9-dimethyl-2,4,8-decatrienal (198 mg, 90%).

후처리

  1. additionwas added to the mixture
  2. customfollowed by removal of the cooling bath and vigorous stirring
  3. customThe resultant while precipitates
  4. filtrationwere filtered
  5. washwashed with n-hexane
  6. stirringstirred for 3 hours
  7. extractionThe organic layer was extracted
  8. customseparated
  9. washwashed with water
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e71dfe02ed7a4998a002c61663dd0167
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05245085

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