Hydrochloric Acid → HCID 11617066, compound

HRID 2113200Notes

Reaction equation

HRID 2113200 reaction equation
[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.[H-].[Na+].Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=1)=[O:16].Cl>C1COCC1.O>[Br:23][C:20]1[CH:21]=[CH:22][C:17]([C:15](=[O:16])[CH2:14][CH:6]2[C:7](=[O:8])[O:9][C:2]([CH3:10])([CH3:1])[O:3][C:4]2=[O:5])=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 74544-Bromophenacyl bromideHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 24758Sodium hydride

Product 1

HCID 11617066HCID 11617066, compoundYield 54.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of Meldrum's acid (5.0 g, 35 mmol) in anhydrous THF (25 mL) was added cautiously to a stirred suspension of sodium hydride (95%, 960 mg, 38 mmol) in anhydrous THF (25 mL). The resulting solution was stirred at room temperature for 1 hr. A solution of 2,4′-dibromoacetophenone (11.6 g, 42 mmol) in anhydrous THF (25 mL) was added dropwise, and the resultant solution was stirred at room temperature for 16-24 hrs (TLC control). The reaction mixture was poured into water (50 mL), acidified to pH 2-3 with 0.5N hydrochloric acid and extracted with ethyl acetate (3×50 mL). The combined extract was washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Trituration and filtration from MeOH afforded the title compound as a white solid (6.56 g).

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. extractionThe combined extract
  3. washwas washed with water, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. filtrationTrituration and filtration from MeOH

Sources & evidence

ORD record
ord-1f8c28dd74944fe5ad2f260048e3d879
Source dataset
uspto-grants-2009_04
Patent number
US07524878B2

Reaction notes

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