Water → 2-(1-Methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenal

HRID 1110174

反応式

HRID 1110174 の反応式
[CH3:1][CH:2]([C:4](=[CH:7][CH:8]=[C:9]([CH3:21])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:20])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])[C:5]#N)[CH3:3].[H-].C([Al+]CC(C)C)C(C)C.O.C(O)(=O)C(O)=[O:35]>CCCCCC.C1(C)C=CC=CC=1>[CH3:1][CH:2]([C:4](=[CH:7][CH:8]=[C:9]([CH3:21])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:20])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])[CH:5]=[O:35])[CH3:3]

参加物

7

反応物 4

HCID 962WaterHCID 971Oxalic AcidHCID 21225700DiisobutylaluminumhydrideHCID 536571452-(1-Methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile

生成物 1

HCID 544419182-(1-Methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenal収率 84%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8058Hexane溶媒3 回

反応条件

温度
-70 °C

実験手順

To a solution of 2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenenitrile (856 mg, 3.0 mmol) in n-hexane (30 ml) was added a 0.5M solution of diisobutylaluminium hydride in toluene (6 ml) with stirring at -70° C. under argon atmosphere. After one hour, water (3 ml) was added, the cooling bath was removed, and the reaction mixture was stirred well. Resultant white precipitates were filtered and washed. The filtrate was concentrated to give a residue, which was dissolved in n-hexane (10 ml). The n-hexane solution was combined with a 10% aqueous solution of oxalic acid (5 ml) and stirred for 3 hours. The organic layer was extracted and separated, washed with water, dried over MgSO4, and concentrated. The resultant residue was subjected to silica gel column chromatography (solvent: n-hexane/ethyl acetate=10:1) to obtain 2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenal (865 mg, 84%).

後処理

  1. customthe cooling bath was removed
  2. stirringthe reaction mixture was stirred well
  3. customResultant white precipitates
  4. filtrationwere filtered
  5. washwashed
  6. concentrationThe filtrate was concentrated
  7. customto give a residue, which
  8. stirringstirred for 3 hours
  9. extractionThe organic layer was extracted
  10. customseparated
  11. washwashed with water
  12. dry with materialdried over MgSO4
  13. concentrationconcentrated

出典と根拠

ORDレコード
ord-44f3e5b21991411fa403ac7f1b688cf9
出典データセット
uspto-grants-1994_06
特許番号
US05324869

関連ノート

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