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

HRID 654587

반응식

HRID 654587 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 935Nickel촉매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a3a8810a229e45fdbdcb3eb59813e1b3
출처 데이터셋
uspto-grants-1992_07
특허 번호
US05132464

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