Ethyl Acetate → HCID 22158154, compound

HRID 1073244Notes

Reaction equation

HRID 1073244 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][CH2:20][CH3:21])[CH:13]=1)([CH3:11])[C:9]#[N:10].C(OCC)(=O)C.[OH-].[Na+]>C1COCC1.CCOCC>[NH2:10][CH2:9][C:8]([CH3:11])([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][CH2:20][CH3:21])[CH:13]=1)[CH3:7]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22158131HCID 22158131, compound

Product 1

HCID 22158154HCID 22158154, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LiAlH4 (1.0 g) in dry THF (25 ml) under dry N2 was added a solution of 2-methyl-2-(3-propyloxyphenyl)propionitrile (1.02 g) in dry THF (10 ml) over 10 minutes. After stirring at 25° for 20 minutes, the reaction mixture was heated under reflux for 5 hours, cooled to 0°, diluted with ether (50 ml) and cautiously decomposed with ethyl acetate (2 ml) followed by 5M NaOH (5 ml). The mixture was filtered and the residue triturated with ether (3×10 ml). The combined filtrates were extracted with 20% HCl (4×10 ml) and the combined extracts basified with 10M NaOH. The liberated oil was extracted into ether (3×15 ml) and the combined extracts dried over Na2SO4, filtered and evaporated to dryness to give a colourless oil.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 5 hours
  3. temperaturecooled to 0°
  4. filtrationThe mixture was filtered
  5. customthe residue triturated with ether (3×10 ml)
  6. extractionThe combined filtrates were extracted with 20% HCl (4×10 ml)
  7. extractionThe liberated oil was extracted into ether (3×15 ml)
  8. dry with materialthe combined extracts dried over Na2SO4
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customto give a colourless oil

Sources & evidence

ORD record
ord-2c045b4849984fb2923b194a71cbb809
Source dataset
uspto-grants-1990_11
Patent number
US04968698

Reaction notes

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