Ethyl Acetate → HCID 71238234, compound

HRID 1402698Notes

Reaction equation

HRID 1402698 reaction equation
[CH2:1]([NH:3][C:4](=[O:6])[CH3:5])[CH3:2].CC(C)([O-])C.[K+].[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1.C(OC(=O)C)C>C1COCC1.O>[Br:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][N:3]([CH2:1][CH3:2])[C:4](=[O:6])[CH3:5])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 12253EthylacetamideHCID 685274-Bromobenzyl bromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 71238234HCID 71238234, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

0.568 mL N-ethylacetamide was dissolved in 20 mL THF. 0.67 g Potassium tert-butoxide was added and the mixture stirred for 20 min at 50° C. Then 1 g of 4-bromobenzylbromide dissolved in 5 mL THF was added and the suspension stirred for 2 h at 50° C. After cooling, ethylacetate and water were added and the organic phase extracted with water (1×), dried and the solvent distilled off. The product was purified via FCC (cyclohexane/ethylacetate: 90/10→50/50) to yield 830 mg N-(4-bromobenzyl)-N-ethylacetamide as an oil.

Workup

  1. additionwas added
  2. stirringthe suspension stirred for 2 h at 50° C
  3. temperatureAfter cooling
  4. extractionthe organic phase extracted with water (1×)
  5. customdried
  6. distillationthe solvent distilled off
  7. customThe product was purified via FCC (cyclohexane/ethylacetate: 90/10→50/50)

Sources & evidence

ORD record
ord-a0f26285adfd49f894f9722dbfd86c97
Source dataset
uspto-grants-2014_12
Patent number
US08912173B2

Reaction notes

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