Water → 14-Chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraen-1-ol

HRID 1609348

反応式

HRID 1609348 の反応式
[Cl:1][CH2:2][C:3]([CH3:25])=[CH:4][CH2:5][CH2:6][C:7]([CH3:24])=[CH:8][CH2:9][CH2:10][C:11]([CH3:23])=[CH:12][CH:13]=[C:14]([CH:20]([CH3:22])[CH3:21])[C:15](OCC)=[O:16].[H-].C([Al+]C(C)C)(C)C.O.CCCCCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[Cl:1][CH2:2][C:3]([CH3:25])=[CH:4][CH2:5][CH2:6][C:7]([CH3:24])=[CH:8][CH2:9][CH2:10][C:11]([CH3:23])=[CH:12][CH:13]=[C:14]([CH:20]([CH3:21])[CH3:22])[CH2:15][OH:16]

参加物

6

反応物 4

HCID 962WaterHCID 21226206Ethyl acetate hexaneHCID 21896610Diisopropylaluminium hydrideHCID 54546229Ethyl 14-chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenoate

生成物 1

HCID 5368470314-Chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraen-1-ol収率 83.7%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

Ethyl 14-chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenoate (670 mg, 1.81 mmol) was dissolved in dry toluene (20 ml) under argon atmosphere. To the solution cooled on an ethanol-dry ice bath was added with stirring 1M diisopropyl aluminium hydride in toluene (4 ml). After 30 minutes, disappearance of the starting material was confirmed. Water (1.5 ml) was added to the reaction mixture, the cooling bath was removed, and the stirring was continued. After further stirring with addition of MgSO4 as a drying agent, the mixture was filtered and condensed. The resulting residue was subjected to silica gel column chromatography (solvent: n-hexane/ethyl acetate (12:1)), and relevant fractions gave 14-chloro-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraen-1-ol (492 mg, 79%).

後処理

  1. temperatureTo the solution cooled on an ethanol-dry ice bath
  2. additionwas added
  3. customthe cooling bath was removed
  4. filtrationthe mixture was filtered
  5. customcondensed

出典と根拠

ORDレコード
ord-39df3b7b91044b489a030a471579f1a6
出典データセット
uspto-grants-1995_03
特許番号
US05399724

関連ノート

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