Ethyl Acetate → HCID 22016838, compound

HRID 1935398Notes

Reaction equation

HRID 1935398 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7](OC)=[O:8])=[CH:5][C:4]=1[O:13][CH3:14])#[N:2].[BH4-].[Li+].CCOC(C)=O>C1COCC1>[C:1]([C:3]1[CH:12]=[CH:11][C:6]([CH2:7][OH:8])=[CH:5][C:4]=1[O:13][CH3:14])#[N:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 4148881Lithium borohydrideHCID 22464400Methyl 4-cyano-3-methoxybenzoate

Product 1

HCID 22016838HCID 22016838, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the ester from Step D (48.8 g, 255 mmol) in 400 mL of dry THF under argon at room temperature was added lithium borohydride (255 mL, 510 mmol, 2M THF) over 5 minutes. After 1.5 hours, the reaction was warmed to reflux for 0.5 hours, then cooled to room temperature. The solution was poured into EtOAc/1N HCl soln. [CAUTION], and the layers were separated. The organic layer was washed with water, sat Na2CO3 soln. and brine (4×), dried (Na2SO4), and concentrated in vacuo to provide the titled product.

Workup

  1. temperaturethe reaction was warmed
  2. temperatureto reflux for 0.5 hours
  3. custom[CAUTION], and the layers were separated
  4. washThe organic layer was washed with water
  5. dry with materialand brine (4×), dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e7add42c4787486dac9cf93adf8b6e9c
Source dataset
uspto-grants-2002_05
Patent number
US06387903B1

Reaction notes

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