Ethyl bromoacetate → HCID 18624153, compound

HRID 1860628Notes

Reaction equation

HRID 1860628 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH3:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:15][CH:14]=1)=[O:12].Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>C1COCC1>[CH2:20]([O:19][C:16]1[CH:15]=[CH:14][C:13]([C:11](=[O:12])[CH:10]([CH3:9])[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:18][CH:17]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 78246p-BenzyloxypropiophenoneHCID 2724682Lithium diisopropylamide

Product 1

HCID 18624153HCID 18624153, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of lithium diisopropylamide (Aldrich, 100 mL, 2M solution in THF) in THF (950 mL) at −78° C. was added a suspension of 4-benzyloxypropiophenone (Lancaster, 50 g) in THF (75 mL) over one minute. After 45 minutes, ethyl bromoacetate (Aldrich, 23 mL) was added during one minute. After one hour, the mixture was allowed to warm to 0° C. over 3 hours. The reaction was quenched with saturated NH4Cl (500 mL). The organic phase was separated and concentrated in vacuo. The residue was purified by chromatography over silica gel using 10% ethyl acetate in hexane as eluant to provide the above compound as a colorless liquid.

Workup

  1. waitAfter one hour
  2. customThe reaction was quenched with saturated NH4Cl (500 mL)
  3. customThe organic phase was separated
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography over silica gel using 10% ethyl acetate in hexane as eluant

Sources & evidence

ORD record
ord-1915292b049f40288379cb6b70b8acb1
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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