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

HRID 1434784

反応式

HRID 1434784 の反応式
[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

反応物 2

HCID 852991(3S)-3-phenylbutanoic acidHCID 178418348HCID 178418348、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

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

  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.)

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

関連ノート

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