Ethyl bromoacetate → HCID 54112137, compound

HRID 258019Notes

Reaction equation

HRID 258019 reaction equation
[OH:1][C:2]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][CH2:12][CH2:13]2)=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:16].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:13]1[C:14]2[C:9](=[C:8]3[C:3](=[C:2]([O:1][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:15]=2)[CH2:4][CH2:5][CH2:6][C:7]3=[O:16])[CH2:10][CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 19782189HCID 19782189, compound

Product 1

HCID 54112137HCID 54112137, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

40.44 g (0.19 mol) of the compound from Example 6 is heated to reflux with 38.64 g (0.23 mol) of ethyl bromoacetate and 31.97 g (0.23 mol) of potassium carbonate in 190 ml of butanone for 5 h. After cooling, the precipitate is filtered off and washed well with acetone and the solution is evaporated. The residue is taken up in 100 ml of CH2Cl2, shaken 3 times with 50 ml of 10% strength NaOH solution each time, dried over Na2SO4 and evaporated. The residue is dried in a high vacuum.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate is filtered off
  3. washwashed well with acetone
  4. customthe solution is evaporated
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue is dried in a high vacuum

Sources & evidence

ORD record
ord-a72c69d34e964755b3612b36d928baf5
Source dataset
uspto-grants-1993_11
Patent number
US05264458

Reaction notes

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