(3E,6R)-6,10-dimethyl-3,9-undecadiene-2-one → (6R)-6,10-dimethylundecan-2-one

HRID 654587

反応式

HRID 654587 の反応式
[CH3:1][C@H:2]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])[CH2:3]/[CH:4]=[CH:5]/[C:6](=[O:8])[CH3:7].[H][H]>C(OCC)(=O)C.[Ni]>[CH3:1][C@H:2]([CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:3][CH2:4][CH2:5][C:6](=[O:8])[CH3:7]

参加物

5

反応物 2

HCID 10965409(3E,6R)-6,10-dimethyl-3,9-undecadiene-2-oneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 1715160(6R)-6,10-dimethylundecan-2-one収率 99.8%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 33.6 g (3E,6R)-6,10-dimethyl-3,9-undecadien-2-one in one liter of ethyl acetate was hydrogenated over Raney-Nickel (2 g) during 21 hours (hydrogen uptake 10.7 l). Thereafter, the catalyst was filtered off and the filtrate was concentrated. According to gas chromatography the crude product (34) contained 77% (R)-6,10-dimethyl-2-undecanone. 15 g of the crude product (44% of the total amount) were chromatographed on silica gel (n-hexane/ethyl acetate). After distillation of the pure fractions there were obtained 8.1 g (R)-6,10-dimethyl-2-undecanone (99.8% purity according to gas chromatography). The enantiomeric purity was 96.6% ee, as determined by gas chromatographic diastereomer analysis of an acetal derivative with an optically active diol. This enantiomeric purity corresponds to that of the used starting material.

後処理

  1. filtrationThereafter, the catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. custom15 g of the crude product (44% of the total amount) were chromatographed on silica gel (n-hexane/ethyl acetate)
  4. distillationAfter distillation of the pure fractions

出典と根拠

ORDレコード
ord-a3a8810a229e45fdbdcb3eb59813e1b3
出典データセット
uspto-grants-1992_07
特許番号
US05132464

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