Ethyl Acetate → HCID 22759289, compound

HRID 1730130Notes

Reaction equation

HRID 1730130 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[O:13][CH2:14][C:15]#[C:16][CH:17]([OH:27])[CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1.C(OCC)(=O)C>CCOCC>[O:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[O:13][CH2:14]/[CH:15]=[CH:16]/[CH:17]([OH:27])[CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 22759318HCID 22759318, compound

Product 1

HCID 22759289HCID 22759289, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Lithium aluminum hydride (7.6 g., 0.2 mole) is dissolved in ether (225 ml.) and 1-(2-tetrahydropyranyloxy)- 4-hydroxy-5-(4-fluorophenoxy)-2-pentyne (35.2 g., 0.12 mole) is added dropwise with stirring during 1.5 hour. The resulting mixture is stirred at 25° for 21 hours and then heated at reflux for 4 hours. The mixture is cooled and treated dropwise with ethyl acetate to consume excess lithium aluminum hydride. It is then poured into 600 ml. of ice-cold 20% aqueous potassium hydroxide solution. The oily product is taken up in ether, washed with water and brine, and dried over magnesium sulfate. Removal of solvent under vacuum leaves the title compound as a yellow residual oil.

Workup

  1. stirringThe resulting mixture is stirred at 25° for 21 hours
  2. temperatureheated
  3. temperatureat reflux for 4 hours
  4. temperatureThe mixture is cooled
  5. customto consume excess lithium aluminum hydride
  6. additionIt is then poured into 600 ml
  7. washwashed with water and brine
  8. dry with materialdried over magnesium sulfate
  9. customRemoval of solvent under vacuum

Sources & evidence

ORD record
ord-71626e27a00443238f6ea062086b83d6
Source dataset
uspto-grants-1976_11
Patent number
US03991106

Reaction notes

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