Ethyl Acetate → HCID 68718116, compound

HRID 1173329Notes

Reaction equation

HRID 1173329 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([N:14]([CH3:16])[CH3:15])=O)=[C:7]([O:17][CH3:18])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOC(C)=O.[OH-].[Na+]>C1COCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][N:14]([CH3:15])[CH3:16])=[C:7]([O:17][CH3:18])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8857Ethyl Acetate2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68716472HCID 68716472, compound

Product 1

HCID 68718116HCID 68718116, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 0.323 g (0.13 mmol) of the product of Step C in 10 mL of anhydrous THF was carefully added 0.1 g (2.63 mmol) of lithium aluminum hydride. The reaction mixture was then stirred overnight under a nitrogen atmosphere at 65° C. The reaction mixture was then cooled using an external ice water bath, 5.0 mL EtOAc was added. The reaction mixture was stirred an additional 20 min, at which point an excess of 2.5 N aqueous sodium hydroxide was added, followed by 50 mL EtOAc. The aqueous layer was separated and re-extracted with EtOAc. The organic layers were combined, dried (Na2SO4), filtered and evaporated in vacuo to afford the title compound.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. additionwas added
  3. customThe aqueous layer was separated
  4. extractionre-extracted with EtOAc
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-69c558bb4c3b44a29f2e2c16e67d1bcc
Source dataset
uspto-grants-2010_11
Patent number
US07834062B2

Reaction notes

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