Phenacyl bromide → HCID 10870609, compound

HRID 1186696Notes

Reaction equation

HRID 1186696 reaction equation
[O:1]=[C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].CC(C)([O-])C.[K+].Br[CH2:22][C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:24]>C1COCC1>[C:2]([CH:3]([CH2:22][C:23](=[O:24])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])(=[O:1])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 7170Ethyl benzoylacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 10870609HCID 10870609, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of ethyl 3-oxo-3-phenylpropanoate 67 (0.754 g, 3.92 mmol) in THF cooled to 0° C. was added potassium tert-butoxide (0.556 g, 4.71 mmol) and the reaction mixture was stirred for 10 minutes followed by the addition of 2-bromo-1-phenylethanone 68 (0.859 g, 4.32 mmol). The reaction mixture was allowed to stir at room temperature for 90 minutes then quenched with ethanol (2) and poured into ethyl acetate and layer separated. The organic layer was washed with water, brine, dried over Na2SO4, then purified by ISCO (40 g column, 0 to 35% ethyl acetate in hexane) to afford compound 69 (0.812 g, 67% yield) as a yellow oil. LRMS (ESI): (calc.) 310.12 (found) 311.08 (MH)+

Workup

  1. stirringto stir at room temperature for 90 minutes
  2. customthen quenched with ethanol (2)
  3. additionpoured into ethyl acetate and layer
  4. customseparated
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over Na2SO4
  7. custompurified by ISCO (40 g column, 0 to 35% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-7529e5cd99184748afdce204b8c471fb
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

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