Ethyl bromoacetate → HCID 54389077, compound

HRID 323204Notes

Reaction equation

HRID 323204 reaction equation
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>O1CCCC1.C(OCC)C.O>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][C:7]([C:8]#[N:9])([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH3:26]

Participants

7

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8794PhenylacetonitrileHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 54389077HCID 54389077, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Combine phenylacetonitrile (175.5 g, 1.5 mol) and tetrahydrofuran (1.95 L). Cool to about 0° C. Add dropwise over about 15 minutes, a solution of sodium bis(trimethylsilyl)amide (3.2 L, 1 M in tetrahydrofuran, 3.2 mol). When the addition is complete, warm the reaction mixture to ambient temperature and allow to stir for 1 hour. Transfer the above solution over about 45 minutes into a cooled (about −20° C.) solution of ethyl bromoacetate (510 g, 3.05 mol) in tetrahydrofuran (1.95 L). Warm to ambient temperature and allow to stir. After 18 hours, dilute with diethyl ether (3 L) and water (1.5 L). Extract twice with saturated aqueous solution of ammonium chloride (2.25 L) and then brine. Dry the organic layer over MgSO4, filter, and concentrate in vacuo to obtain a residue. Distill the residue by bulb-to-bulb distillation to give the title compound: bp; 180-190° C. at 30 mm of Hg. Elemental Analysis calculated for C16H19NO4: C, 66.43; H, 6.62; N, 4.84. Found: C, 66.34; H, 6.57; N, 4.82.

Workup

  1. additionAdd dropwise over about 15 minutes
  2. additionWhen the addition
  3. temperaturewarm the reaction mixture to ambient temperature
  4. customover about 45 minutes
  5. temperatureWarm to ambient temperature
  6. stirringto stir
  7. waitAfter 18 hours
  8. extractionExtract twice with saturated aqueous solution of ammonium chloride (2.25 L)
  9. dry with materialDry the organic layer over MgSO4
  10. filtrationfilter
  11. concentrationconcentrate in vacuo
  12. customto obtain a residue
  13. distillationDistill the residue
  14. distillationby bulb-to-bulb distillation

Sources & evidence

ORD record
ord-2b5c00282bdb40e2909a685408be1acd
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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