Dichloromethane → (S)-6-methyl-5-decanone

HRID 364333

반응식

HRID 364333 반응식
[Cl-].[Cl-].[CH2:3]([Al+2])[CH3:4].[CH2:6](Cl)Cl.[CH2:9]([C:13]([OH:25])([CH2:21][CH2:22][CH2:23][CH3:24])[C@@H](OS(C)(=O)=O)C)[CH2:10][CH2:11]C>P(=O)(O)(O)O.C(OCC)(=O)C>[CH3:6][C@@H:9]([CH2:10][CH2:11][CH2:3][CH3:4])[C:13](=[O:25])[CH2:21][CH2:22][CH2:23][CH3:24]

참가 물질

6

반응물 3

HCID 6344DichloromethaneHCID 13349244(S)-3-butyl-2-methanesulfonyloxy-3-heptanolHCID 16686341Ethyl aluminium dichloride

생성물 1

HCID 13349250(S)-6-methyl-5-decanone수율 87%

시약·촉매·용매 2

HCID 1004Phosphoric Acid촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

After 0.95 ml (0.95 mmol) of ethylaluminum dichloride (hexane 1M solution) were added to a dried methylene chloride (3 ml) solution of 101.5 mg (0.38 mmol) of (S)-3-butyl-2-methanesulfonyloxy-3-heptanol (unrefined) at -78° C. under stirring, and stirred for two and a half hours at -78° C., the temperature was raised to 0° C. over an hour and a half. The reaction was stopped with three drops of phosphoric acid buffer solution (pH 7). The resultant suspension was diluted with ethyl acetate, dried with anhydrous sodium sulfate, filtered and concentrated. The oily residue was separated and refined by the use of silica gel column chromatography (hexane/ethyl acetate=35/1) to obtain (S)-6-methyl-5-decanone as a pale yellow oily substance (56.3 mg, yield 87%).

후처리

  1. stirringstirred for two and a half hours at -78° C.
  2. dry with materialdried with anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe oily residue was separated

출처 및 근거

ORD 기록
ord-5753457797da46cc8cf472f5691cd339
출처 데이터셋
uspto-grants-1986_08
특허 번호
US04604486

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