1-Acetoxy-2-bromoethane → HCID 59389387, compound

HRID 2357914Notes

Reaction equation

HRID 2357914 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[CH:20]=[C:8]2[C:9]([C:13](=[O:19])[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:11]=[CH:12][N:7]2[N:6]=1)[CH3:4].[C:21]([O:24][CH2:25][CH2:26]Br)(=[O:23])[CH3:22].[Cl-].[NH4+]>CN(C)C=O>[CH2:3]([C:5]1[CH:20]=[C:8]2[C:9]([C:13](=[O:19])[CH:14]([C:15]([O:17][CH3:18])=[O:16])[CH2:22][C:21]([O:24][CH2:25][CH3:26])=[O:23])=[CH:10][CH:11]=[CH:12][N:7]2[N:6]=1)[CH3:4]

Participants

6

Reactant 4

HCID 135641-Acetoxy-2-bromoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59389405HCID 59389405, compound

Product 1

HCID 59389387HCID 59389387, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60% sodium hydride (135 mg) was added to a solution of the compound of Example 180 (830 mg) in N,N-dimethylformamide (40 mL) in a stream of argon gas while the solution was stirred in an ice bath. The mixture was then stirred at room temperature for 15 min. Subsequently, bromoethyl acetate (374 μL) was added to the mixture under stirring in an ice bath. The mixture was further stirred at room temperature for 3 hours. Subsequently, a saturated aqueous solution of ammonium chloride was added and the mixture was extracted with ethyl acetate. The organic layer was washed sequentially with water (×2) and saturated brine and dried over anhydrous sodium sulfate. Evaporation of the solvent and subsequent purification by silica gel column chromatography (hexane:ethyl acetate=2:1) afforded the title compound as a mixture with o-alkylated form. This product was used in the subsequent reaction without further purification.

Workup

  1. stirringThe mixture was then stirred at room temperature for 15 min
  2. stirringunder stirring in an ice bath
  3. stirringThe mixture was further stirred at room temperature for 3 hours
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed sequentially with water (×2) and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customEvaporation of the solvent and subsequent purification by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-ed1442d3899e49ae9040f5764ca02815
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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