Ethyl Acetate → (4S)-Oct-1-yn-4-ol

HRID 2049249Notes

Reaction equation

HRID 2049249 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-b4ee4cfe54774bb4b457d22400398ff6
Source dataset
uspto-grants-1980_04
Patent number
US04197245

Reaction notes

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