Ethyl bromoacetate → HCID 20495240, compound

HRID 1074905Notes

Reaction equation

HRID 1074905 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[O:17][CH2:16][CH2:15][CH2:14][C:13]=2[CH:12]=[C:11]([OH:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>CC(C)=O>[CH2:1]([O:8][C:9]1[C:18]2[O:17][CH2:16][CH2:15][CH2:14][C:13]=2[CH:12]=[C:11]([O:19][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 20495242HCID 20495242, compound

Product 1

HCID 20495240HCID 20495240, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.82 g of 8-benzyloxy-3,4-dihydro-6-hydroxy-2H-1-benzopyran (0.82 g) was dissolved in 300 ml of anhydrous acetone, and 0.88 g of anhydrous potassium carbonate and 1.07 g of ethyl bromoacetate were added. The mixture was stirred under reflux for 7 hours. After the reaction, the insoluble matter was removed by filtration, and the solvent was distilled off. The residue was dissolved in 50 ml of chloroform, washed with water and dried. The solvent was distilled off to give 1.09 g (yield 99.5%) of 8-benzyloxy-3,4-dihydro-6-ethoxycarbonylmethoxy-2H-1-benzopyran.

Workup

  1. temperatureunder reflux for 7 hours
  2. customAfter the reaction
  3. customthe insoluble matter was removed by filtration
  4. distillationthe solvent was distilled off
  5. dissolutionThe residue was dissolved in 50 ml of chloroform
  6. washwashed with water
  7. customdried
  8. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-1340ab3c2c7948219db09babadffbeba
Source dataset
uspto-grants-1983_07
Patent number
US04394382

Reaction notes

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