Ethyl Bromide → 53692-88-9

HRID 2234471Notes

Reaction equation

HRID 2234471 reaction equation
[CH3:1][O:2][C:3](=[O:7])[CH2:4][C:5]#[N:6].[CH2:8]1CCN2C(=NCCC2)C[CH2:9]1.[CH2:19](Br)[CH3:20]>C1COCC1>[CH3:1][O:2][C:3](=[O:7])[C:4]([C:5]#[N:6])([CH2:19][CH3:20])[CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 7747Methyl cyanoacetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 1234993153692-88-9Yield 64.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Methylcyanoacetate (Aldrich; 20 g, 0.201 mol) was dissolved in THF (250 mL), to this was added DBU (75 mL, 0.505 mol) and ethyl bromide (40 mL, 0.606 mol). The reaction was stirred at 50° C. for 2 hours before being cooled and quenched with sat NH4Cl(aq). The organic layer was separated and the remaining aqueous was extracted with diethyl ether (2×100 mL), dried and solvent removed in vacuo to yield yellow oil. Purification was achieved via distillation at 70° C. at 0.5 mbar to afford methyl2-cyano-2-ethyl-butanoate as a clear oil (20 g, 0.129 mol) which was reduced with hydrogen under pressure using Raney nickel catalyst (2 g). The reaction mixture was filtered and solvent evaporated to the title compound as a slightly dark oil. (16 g, 50%).

Workup

  1. temperaturebefore being cooled
  2. customquenched with sat NH4Cl(aq)
  3. customThe organic layer was separated
  4. extractionthe remaining aqueous was extracted with diethyl ether (2×100 mL)
  5. customdried
  6. customsolvent removed in vacuo
  7. customto yield yellow oil
  8. customPurification
  9. distillationwas achieved via distillation at 70° C. at 0.5 mbar

Sources & evidence

ORD record
ord-931562dc6f064bf1a086d29fc3a5b915
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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