(3S)-3-phenylbutanoic acid → (S)-4-Phenylpentan-2-one

HRID 1434784

반응식

HRID 1434784 반응식
[CH3:1][Li].[C:3]1([C@@H:9]([CH3:14])[CH2:10][C:11]([OH:13])=O)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CCOCC>[C:3]1([C@@H:9]([CH3:14])[CH2:10][C:11](=[O:13])[CH3:1])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

참가 물질

4

반응물 2

HCID 852991(3S)-3-phenylbutanoic acidHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 11008238(S)-4-Phenylpentan-2-one

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

1.6 M Methyl lithium (17.8 mL, 24.9 mmol) was added over 1 hour to a stirring 0° C. solution of (S)-3-Phenylbutyric acid (2.0147 g, 12.18 mmol) in dry Et2O (61 mL, 0.2 M): The ice bath was removed, and the reaction was allowed to stir at room temperature for 1½ additional hours. The reaction was then poured into rapidly stirring ice water containing aq. HCl. The organic layer was removed, washed with NaHCO3 and brine, then dried with Na2SO4, filtered and concentrated to achieve pure 77 (2.0487 g, (2.0487 g, ˜100%): HPLC: 10.081 min. (Note: SM has HPLC retention time of 9.127 min.)

후처리

  1. customThe ice bath was removed
  2. additionThe reaction was then poured into rapidly stirring ice water containing aq. HCl
  3. customThe organic layer was removed
  4. washwashed with NaHCO3 and brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custom10.081 min. (Note: SM has HPLC retention time of 9.127 min.)

출처 및 근거

ORD 기록
ord-450a6a0a066d4b289bbc11c762721b29
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07615572B2

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