Ethyl Acetate → (4S)-Oct-1-yn-4-ol

HRID 261374ノート

反応式

HRID 261374 の反応式
C([O:9][C@@H:10]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:11][C:12]#[CH:13])(=O)C1C=CC=CC=1.[OH-].[K+].OC(CCCC)CC#C.C(OCC)(=O)C>CO.O>[OH:9][C@@H:10]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:11][C:12]#[CH:13]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 1036561-Octyn-4-olHCID 53798844HCID 53798844、化合物

生成物 1

HCID 12786164(4S)-Oct-1-yn-4-ol

試薬・触媒・溶媒 1

HCID 22242641Methanol--water (1/1)溶媒

実験手順

A solution of 1.15 g (5.0 mmoles) of (S)-4-benzoyloxy-1-octyne (Example 141) and 1.40 g (25 mmoles) of potassium hydroxide in 50 ml of 10:1 methanol-water is allowed to stand at room temperature for 24 hours. The bulk of the methanol is evaporated at room temperature, and the mixture is extracted with ether. The extract is washed with brine, dried over magnesium sulfate, and evaporated to give a colorless oil, identical to 4-hydroxy-1-octyne [α]D25 =+17+1.0° (C=0.77, ethyl acetate). This compound has the (S)-configuration.

後処理

  1. customThe bulk of the methanol is evaporated at room temperature
  2. extractionthe mixture is extracted with ether
  3. washThe extract is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto give a colorless oil

出典と根拠

ORDレコード
ord-ad11f6da20d9444c859442db9c3eadfb
出典データセット
uspto-grants-1979_08
特許番号
US04165331

反応ノート

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