Potassium Hydroxide → (4S)-Oct-1-yn-4-ol

HRID 1448366Notes

Reaction equation

HRID 1448366 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+].CO.O.OC(CCCC)CC#C>C(OCC)(=O)C>[OH:9][C@@H:10]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:11][C:12]#[CH:13]

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 1036561-Octyn-4-olHCID 22242641Methanol--water (1/1)HCID 53798844(S)-4-benzoyloxy-1-octyne

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.15 g. (5.0 mmoles) of (S)-4-benzoyloxy-1-octyne (Example 618) 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-95d1c22f460a48eeabf6f515fb0e5c5c
Source dataset
uspto-grants-1979_12
Patent number
US04179451

Reaction notes

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