Ethyl bromoacetate → HCID 17937805, compound

HRID 1828648Notes

Reaction equation

HRID 1828648 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[O:6][CH2:7][C:8](=[O:9])[C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18]([O:20][C:21](=[O:24])[CH2:22]Br)[CH3:19].CCCCCC>O1CCCC1.C(OCC)(=O)C>[CH2:18]([O:20][C:21]([CH2:22][O:1][C:2]1[CH:11]=[CH:10][C:5]2[O:6][CH2:7][C:8](=[O:9])[C:4]=2[CH:3]=1)=[O:24])[CH3:19]

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8058HexaneHCID 11430Potassium CarbonateHCID 99641425-Hydroxy-1-benzofuran-3(2H)-one

Product 1

HCID 17937805HCID 17937805, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.00 g (20 mmol) XVIII, 3.96 g (40 mmol) K2CO3 and 5.54 ml (50 mmol) bromoacetic acid ethyl ester were heated under reflux for 72 h in 150 ml tetrahydrofuran. After filtration, the solvent was removed. Flash chromatography (200 g SiO2, n-hexane:ethyl acetate=2:1) produced 4.63 g (19.6 mmol, 98%) XIX.

Workup

  1. filtrationAfter filtration
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-1c29ef35659044f586a51410615201bc
Source dataset
uspto-grants-2006_06
Patent number
US07060109B2

Reaction notes

Loading…