Ethyl Acetate → (4S)-Oct-1-yn-4-ol

HRID 2083517Notes

Reaction equation

HRID 2083517 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 (45 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-8ae8a95be5ef448492f1edff5bcb4d79
Source dataset
uspto-grants-1978_04
Patent number
US04085272

Reaction notes

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