(3S)-3-phenylbutanoic acid → (S)-4-Phenylpentan-2-one
反応式
[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]=1参加物
4
実験手順
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.)
後処理
- customThe ice bath was removed
- additionThe reaction was then poured into rapidly stirring ice water containing aq. HCl
- customThe organic layer was removed
- washwashed with NaHCO3 and brine
- dry with materialdried with Na2SO4
- filtrationfiltered
- concentrationconcentrated
- custom10.081 min. (Note: SM has HPLC retention time of 9.127 min.)
出典と根拠
- ORDレコード
- ord-450a6a0a066d4b289bbc11c762721b29
- 出典データセット
- uspto-grants-2009_11
- 特許番号
- US07615572B2
反応ノート
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