Ethyl Acetate → HCID 19014485, compound

HRID 248040Notes

Reaction equation

HRID 248040 reaction equation
[C:1]1([NH:7][C:8](=O)[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.[OH-].[Na+]>O1CCCC1>[C:1]1([NH:7][CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:13][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 19014751HCID 19014751, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19014485HCID 19014485, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 0° C. suspension of 21.0 g of product from Example 144 in 200 ml of dry tetrahydrofuran is added, dropwise over 30 minutes, 51.27 ml of 1M solution of lithium aluminum hydride in tetrahydrofuran. The reaction is stirred at room temperature for 1 hour, heated at reflux temperature for 2 hours and stirred overnight at room temperature. Ethyl acetate is added followed by concentrated sodium hydroxide. The reaction is filtered, concentrated in vacuo and the residue is recrystallized from hexane to give 16.9 g of the desired product.

Workup

  1. additionis added, dropwise over 30 minutes
  2. temperatureheated
  3. temperatureat reflux temperature for 2 hours
  4. stirringstirred overnight at room temperature
  5. filtrationThe reaction is filtered
  6. concentrationconcentrated in vacuo
  7. customthe residue is recrystallized from hexane

Sources & evidence

ORD record
ord-01a952894ec744489aa1dab721cd5b0c
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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