Diethyl Ether → geranylcitronellol

HRID 1589533ノート

反応式

HRID 1589533 の反応式
C(OCC)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:12][CH:13]([CH2:18][CH2:19]/[CH:20]=[C:21](\[CH3:33])/[CH2:22][CH2:23]/[CH:24]=[C:25](\[CH3:32])/[CH2:26][CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])[CH2:14][C:15](O)=[O:16].C(OCC)(=O)C>O>[CH3:12][CH:13]([CH2:18][CH2:19]/[CH:20]=[C:21](\[CH3:33])/[CH2:22][CH2:23]/[CH:24]=[C:25](\[CH3:32])/[CH2:26][CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])[CH2:14][CH2:15][OH:16]

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 12837064(E,E)-3,7,11,15-tetramethyl-6,10,14-hexadecatrienoic acidHCID 21226445Aluminium lithium hydride

生成物 1

HCID 5365870geranylcitronellol

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
10 °C

実験手順

To 150 ml. of anhydrous diethyl ether there was added 1.9 g. of lithium aluminum hydride. To the mixture was dropwise added, under stirring and at 10° C., 1.53 g. of the carboxylic acid compound obtained in Example 1. The resulting mixture was then stirred at room temperature for 1 hour, and 1 ml. of ethyl acetate and 1 ml. of water were then added thereto. The mixture was subsequently washed with water and dried. The solvent was removed by evaporation and the resulting residual oil was purified by silica gel column chromatography to obtain 13.8 g. of the desired oily product.

後処理

  1. additionTo the mixture was dropwise added
  2. stirringThe resulting mixture was then stirred at room temperature for 1 hour
  3. washThe mixture was subsequently washed with water
  4. customdried
  5. customThe solvent was removed by evaporation
  6. customthe resulting residual oil was purified by silica gel column chromatography
  7. customto obtain 13.8 g

出典と根拠

ORDレコード
ord-d27af73eb17241988ee4120a30322015
出典データセット
uspto-grants-1986_02
特許番号
US04571408

反応ノート

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