Ethyl bromoacetate → HCID 19421373, compound

HRID 743997Notes

Reaction equation

HRID 743997 reaction equation
[H-].[Na+].[CH2:3]([C:7]1[N:8]([O:23][CH2:24][O:25][CH:26]([Si:28]([CH3:31])([CH3:30])[CH3:29])[CH3:27])[C:9]([C:12](=[O:22])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=2[OH:21])=[CH:10][N:11]=1)[CH2:4][CH2:5][CH3:6].Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]>CN(C=O)C>[CH2:3]([C:7]1[N:8]([O:23][CH2:24][O:25][CH:26]([Si:28]([CH3:30])([CH3:29])[CH3:31])[CH3:27])[C:9]([C:12](=[O:22])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=2[O:21][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:10][N:11]=1)[CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 19421374HCID 19421374, compound

Product 1

HCID 19421373HCID 19421373, compoundYield 93,750.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of NaH (80% oil dispersion, 33 mg, 1.1 mmol, previously washed with hexanes), in DMF (4 ml) was added dropwise a solution of 2-n-butyl-5-(2-Hydroxy-4-methoxybenzoyl)-1-trimethylsilylethyloxymethoxy-1H-imidazole-(404 mg, 1.00 mmol) in DMF (3 ml) at 0° under argon. The cooling bath was removed and the mixture stirred for 10 min. at ambient temperature. Ethyl bromoacetate (125 μl, 1.10 mmol) was added neat and the reaction stirred for 2 h. The mixture was partitioned between water and EtOAc and the layers separated. The aqueous layer was further extracted (EtOAc, 2x) and the combined organic extract was washed with water (5x) and brine. Evaporation under reduced pressure, after drying (MgO4 anhydrous) afforded the title compound as a reddish oil (475 g, 97%).

Workup

  1. washpreviously washed with hexanes), in DMF (4 ml)
  2. customThe cooling bath was removed
  3. stirringthe reaction stirred for 2 h
  4. customThe mixture was partitioned between water and EtOAc
  5. customthe layers separated
  6. extractionThe aqueous layer was further extracted (EtOAc, 2x)
  7. extractionthe combined organic extract
  8. washwas washed with water (5x) and brine
  9. customEvaporation under reduced pressure
  10. customafter drying (MgO4 anhydrous)

Sources & evidence

ORD record
ord-966d6ca0eaa743c5ad3ef7dc92506758
Source dataset
uspto-grants-1996_09
Patent number
US05559105

Reaction notes

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