Ethyl bromoacetate → HCID 54141084, compound

HRID 326315Notes

Reaction equation

HRID 326315 reaction equation
[OH:1][C:2]1[CH:16]=[C:15]([OH:17])[CH:14]=[C:13]2[C:3]=1[C:4](=[O:18])[CH2:5][C:6]1([NH:12]2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:1][C:2]1[CH:16]=[C:15]([O:17][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:14]=[C:13]2[C:3]=1[C:4](=[O:18])[CH2:5][C:6]1([NH:12]2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 19736714HCID 19736714, compound

Product 1

HCID 54141084HCID 54141084, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5,7-dihydroxyspiro[1,2,3,4-tetrahydroquinoline-2,1'-cyclohexan]-4-one (prepared in Preparation 81) (0.247 g, 1.0 mmol), ethyl bromoacetate (0.184 g, 1.10 mmol), anhydrous potassium carbonate (0.207 g, 1.5 mmol), and dry acetonitrile (4 ml) is stirred at room temperature for 4 hours. The solvent is removed under reduced pressure and the residue is extracted with ethyl acetate and water. The ethyl acetate layer is separated, washed with water, dried, and the solvent is removed. The residue is placed on a silica gel column and eluted with a mixture of acetone and dichloromethane (1:10) to obtain a crude product. Recrystallization from a mixture of diethyl ether and hexane gives ethyl 2-{(5-hydroxy-4-oxospiro [1,2,3,4-tetrahydroquinoline-2,1'-cyclohexan]-7-yl)oxy}acetate (0.265 g, 79%, m.p.=134°-135° C.).

Workup

  1. customThe solvent is removed under reduced pressure
  2. extractionthe residue is extracted with ethyl acetate and water
  3. customThe ethyl acetate layer is separated
  4. washwashed with water
  5. customdried
  6. customthe solvent is removed
  7. washeluted with a mixture of acetone and dichloromethane (1:10)
  8. customto obtain a crude product
  9. customRecrystallization
  10. additionfrom a mixture of diethyl ether and hexane

Sources & evidence

ORD record
ord-5e0708e003684dd29572c494b6c3fcb7
Source dataset
uspto-grants-1993_12
Patent number
US05268386

Reaction notes

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