Dimethyl Sulfide → 2-Carbomethoxymethyl-5-ethenyl-2-ethylcyclohexanone

HRID 483131노트

반응식

HRID 483131 반응식
[C:1]([CH2:5][C:6]1([CH2:13][CH3:14])[C:11](=[O:12])[CH:10]=[CH:9][CH2:8][CH2:7]1)([O:3][CH3:4])=[O:2].S(C)C.[CH:18]([Mg]Br)=[CH2:19]>C1COCC1>[C:1]([CH2:5][C:6]1([CH2:13][CH3:14])[CH2:7][CH2:8][CH:9]([CH:18]=[CH2:19])[CH2:10][C:11]1=[O:12])([O:3][CH3:4])=[O:2]

참가 물질

5

반응물 3

HCID 1068Dimethyl Sulfide2회HCID 136492416-Carbomethoxymethyl-6-ethyl-2-cyclohexen-1-oneHCID 178418507HCID 178418507, 화합물

생성물 1

HCID 142014342-Carbomethoxymethyl-5-ethenyl-2-ethylcyclohexanone수율 69%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The enone, 6-carbomethoxymethyl-6-ethyl-2-cyclohexen-1-one, prepared by the process of Step (c) (58.1 mmol, 11.4 g), 5.81 mmol (1.194 g) of CuBr.Me2S and 11.7 ml of Me2S were stirred in 176 ml of THF at -40° C. under nitrogen and treated with 58.1 mmol (58.1 ml of 1M solution in THF) of vinylmagnesium bromide added dropwise over 45 minutes. The reaction was then quenched with 200 ml of 1M HCl (aq.) and extracted with 5×100 ml of petroleum ether. Drying (MgSO4) and flash chromatography afforded 8.96 g (39.9 mmol, 69% pale yellow oil) of product as a mixture of diastereomers. The diastereomers (56:44 ratio) were separated by preparative HPLC on a Prep 500A using a brand of silica gel available from Waters Associates, Milford, Ma., and designated "more polar isomer" and "less polar isomer."

후처리

  1. additionadded dropwise over 45 minutes
  2. customThe reaction was then quenched with 200 ml of 1M HCl (aq.)
  3. extractionextracted with 5×100 ml of petroleum ether
  4. dry with materialDrying (MgSO4) and flash chromatography

출처 및 근거

ORD 기록
ord-79d499814b2341afa98bdcffec7ad545
출처 데이터셋
uspto-grants-1986_03
특허 번호
US04578398

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