Ethyl bromoacetate → HCID 6618951, compound

HRID 326299Notes

Reaction equation

HRID 326299 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:15][C:9]3([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]3)[CH2:8][C:7](=[O:16])[C:6]=2[CH:17]=1.Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:16]=[C:7]1[C:6]2[CH:17]=[C:2]([O:1][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:3]=[CH:4][C:5]=2[O:15][C:9]2([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH2:8]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 3243908HCID 3243908, compound

Product 1

HCID 6618951HCID 6618951, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-hydroxy-spiro[2H-1-benzopyran-2,1'-cyclohexan]-4(3H)-one (prepared in Preparation 14) (0.878 g, 3.78 mmol), ethyl bromoacetate (0.69 g, 4.13 mmol), anhydrous potassium carbonate (0.78 g, 5.65 mmol) and dry N,N-dimethylformamide (DMF) (7.5 ml) is stirred at room temperature for 4 hours under nitrogen gas. DMF is removed by distillation under reduced pressure and the residue is extracted with diethyl ether. The ether layer is separated and washed successively with water, dilute sodium hydroxide and saturated brine, dried and distilled to remove ether. The residue is recrystallized from cyclohexane to obtain the title compound as a crystalline solid (1.11 g, yield 92.5%, m.p=72°-73° C.). ##STR10##

Workup

  1. customDMF is removed by distillation under reduced pressure
  2. extractionthe residue is extracted with diethyl ether
  3. customThe ether layer is separated
  4. washwashed successively with water, dilute sodium hydroxide and saturated brine
  5. customdried
  6. distillationdistilled
  7. customto remove ether
  8. customThe residue is recrystallized from cyclohexane

Sources & evidence

ORD record
ord-0b50743f4741405e91065ebf23dfc188
Source dataset
uspto-grants-1993_12
Patent number
US05268386

Reaction notes

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