Sodium hydride → HCID 10546091, compound

HRID 400299Notes

Reaction equation

HRID 400299 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](Cl)=[O:12])=[CH:6][CH:5]=1.[OH2:14].[CH3:15][CH2:16][O:17][C:18]([CH3:20])=[O:19]>C1(C)C=CC=CC=1>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([CH:20]([C:6](=[O:14])[CH:7]([CH3:10])[CH3:8])[C:18]([O:17][CH2:16][CH3:15])=[O:19])=[O:12])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 181552Benzeneacetyl chloride, 4-bromo-HCID 22728543Water ethylacetate

Product 1

HCID 10546091HCID 10546091, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

To a suspension of NaH (7.6 g, 158 mmol) in toluene (142 mL) at 0° C. was added dropwise a solution of ethyl isobutylylacetate (20 g, 126 mmol) in toluene (52 mL) and the resulting solution was stirred under an argon atmosphere for 30 min. Then, a solution of 4-bromophenylacetyl chloride (29.4 g, 126 mmol, prepared as described in reference example 1) in toluene (98 mL) was slowly added and the reaction mixture stirred at room temperature overnight. The resulting solution was poured into H2O-EtOAc and extracted with H2O (2×). The organic phase was washed with brine, the aqueous phase was acidified and extracted with EtOAc, and the combined organic phases were dried and concentrated. The residue was chromatographed on silica gel (hexane-EtOAc, 5%) to afford the title compound (29 g, 65%).

Workup

  1. stirringthe reaction mixture stirred at room temperature overnight
  2. extractionextracted with H2O (2×)
  3. washThe organic phase was washed with brine
  4. extractionextracted with EtOAc
  5. customthe combined organic phases were dried
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel (hexane-EtOAc, 5%)

Sources & evidence

ORD record
ord-3194903743c5487f85bcd3797cc1ec6c
Source dataset
uspto-grants-1998_10
Patent number
US05827863

Reaction notes

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