Ethyl Acetate → HCID 54263880, compound

HRID 1193622Notes

Reaction equation

HRID 1193622 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([CH3:29])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]#[C:19]OC(=O)C3C=CC=CC=3)[CH:16]=2)[O:11][CH2:10][CH2:9]1.[H-].C([O:34][CH2:35][CH3:36])(=O)C.[Cl-].[NH4+]>C(OCC)C>[CH3:29][C:8]1([CH3:7])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]#[C:19][C:8]3[CH:17]=[CH:16][C:36]([CH2:35][OH:34])=[CH:10][CH:9]=3)[CH:16]=2)[O:11][CH2:10][CH2:9]1

Participants

7

Reactant 5

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 166653HydrideHCID 21226445Aluminium lithium hydrideHCID 86742790HCID 86742790, compound

Product 1

HCID 54263880HCID 54263880, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-65 °C

Procedure

A 250 ml 3-necked flask is fitted with a stirrer, a dripping funnel, a nitrogen inlet and a thermometer. In the flask is placed a solution of 379.5 mg (10 mmol) of lithium aluminum hydride in 30 ml of dry diethyl ether. The solution is cooled to -65° C. under nitrogen and a solution of 3.3441 g (10 mmol) of ethyl-4-((4,4-dimethylchroman-6-ylethynyl)benzoate in 15 ml of dry ether is added dropwise at a rate such that the temperature does not exceed -60° C. The mixture is stirred at -30° C. for 1 hour and the excess hydride is then destroyed by the addition of 300 mg (3.4 mmol) of ethyl acetate. The reaction mixture is then hydrolyzed by adding 3 ml of saturated ammonium chloride solution and allowing the temperature to rise to room temperature. The mixture is then filtered and the residue washed with ether. The ether layer is then washed with saturated sodium chloride solution, dried (MgSO4) and then concentrated in vacuo. The residue is purified by chromatography followed by recrystallization to give the title compound.

Workup

  1. customA 250 ml 3-necked flask is fitted with a stirrer, a dripping funnel, a nitrogen inlet
  2. customdoes not exceed -60° C
  3. customto rise to room temperature
  4. filtrationThe mixture is then filtered
  5. washthe residue washed with ether
  6. washThe ether layer is then washed with saturated sodium chloride solution
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue is purified by chromatography
  10. customfollowed by recrystallization

Sources & evidence

ORD record
ord-ca5f2f59863242819afd0d2a4acada23
Source dataset
uspto-grants-1989_03
Patent number
US04810804

Reaction notes

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