Ethyl Acetate → 2-(2-Chlorophenyl)-1-phenylethan-1-one

HRID 401147Notes

Reaction equation

HRID 401147 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9](N(OC)C)=[O:10].[C:15]1([Mg]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCOC(C)=O>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 46318635HCID 46318635, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 936812-(2-Chlorophenyl)-1-phenylethan-1-oneYield 14.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(2-chlorophenyl)-N-methoxy-N-methylacetamide (0.51 g, 2.4 mmol) in anhydrous THF (10 mL) cooled to −78° C., a solution of phenylmagnesium bromide (1 mol/L, 3.5 mL) in THF was added. The reaction mixture was stirred at this temperature for five hours. TLC (PE:EtOAc=10:1) indicated that 50% of the starting materials were consumed. H2O (10 mL) was added to quench the reaction, and the aqueous layer extracted with EtOAc (10 mL×3). The combined organic layer was washed with brine (10 mL), dried over Na2SO4, filtered, concentrated, and purified by column chromatography (PE:EtOAc=50:1) to afford Intermediate 10 as a colorless oil (80 mg, yield: 14.8%).

Workup

  1. customwere consumed
  2. additionH2O (10 mL) was added
  3. customto quench
  4. customthe reaction
  5. extractionthe aqueous layer extracted with EtOAc (10 mL×3)
  6. washThe combined organic layer was washed with brine (10 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by column chromatography (PE:EtOAc=50:1)

Sources & evidence

ORD record
ord-bbf7540d72c648cda5e25fb937b72ee6
Source dataset
uspto-grants-2014_06
Patent number
US08741915B2

Reaction notes

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