Ethyl Acetate → (4S)-Oct-1-yn-4-ol

HRID 848857Notes

Reaction equation

HRID 848857 reaction equation
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]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 1036561-Octyn-4-olHCID 53798844(S)-4-benzoyloxy-1-octyne

Product 1

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

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fad7252c93d24a97aff7729c1b0a4c14
Source dataset
uspto-grants-1981_10
Patent number
US04297516

Reaction notes

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