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

HRID 5664

反応式

HRID 5664 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8058Hexane溶媒

反応条件

温度
-70 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-e71dfe02ed7a4998a002c61663dd0167
出典データセット
uspto-grants-1993_09
特許番号
US05245085

関連ノート

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