Water → HCID 21955999, compound

HRID 2212883Notes

Reaction equation

HRID 2212883 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[CH3:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[CH:9]=1)=[O:7].C1COCC1.O>CCOC(C)=O.ClCCl>[Br:14][C:10]1[CH:9]=[C:8]([C:6](=[O:7])[CH2:5][C:2](=[O:1])[CH3:3])[CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 165023'-BromoacetophenoneHCID 2723922Sodium ethoxide

Product 1

HCID 21955999HCID 21955999, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-5 °C

Procedure

To a suspension of sodium ethoxide (3.82 g, 55 mmol) in EtOAc (10 mL) that was cooled to −5° C. was added a solution of 3-bromoacetophenone (10.0 g, 50 mmol) in EtOac (10 mL) and THF (10 mL). The mixture was stirred at 0° C. for 4 hours before warming to ambient temperature and stirring for 48 hours. Water (20 mL) and dichloromethane (40 mL) were added. The aqueous layer was separated, and acidified to pH 1 by addition of 2N HCl. EtOAc (100 mL) was added and separated, and the water was washed with EtOAc (2×100 mL). The organic portions were combined, dried (Na2SO4) and concentrated in vacuo to yield title compound as a beige, waxy solid (9.57 g, 79%).

Workup

  1. temperaturebefore warming to ambient temperature
  2. stirringstirring for 48 hours
  3. customThe aqueous layer was separated
  4. additionacidified to pH 1 by addition of 2N HCl
  5. additionEtOAc (100 mL) was added
  6. customseparated
  7. washthe water was washed with EtOAc (2×100 mL)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e79c9dca9ce944a4886718551c191ef6
Source dataset
uspto-grants-2006_09
Patent number
US07105518B2

Reaction notes

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