Ethyl Acetate → (4S)-Oct-1-yn-4-ol

HRID 262883

반응식

HRID 262883 반응식
C([O:9][CH: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]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 1036561-Octyn-4-olHCID 204420544-Benzoyloxy-1-octyne

생성물 1

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

시약·촉매·용매 1

HCID 22242641Methanol--water (1/1)용매

실험 절차

A solution of 1.15 g (5.0 mmoles) of (S)-4-benzoyl-oxy-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.

후처리

  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

출처 및 근거

ORD 기록
ord-047c85d251bc4435a0923f61a79e2469
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04154954

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