Dabco → HCID 22287783, compound

HRID 968149Notes

Reaction equation

HRID 968149 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[Br:15][CH:16]([C:20](Br)([CH3:24])[C:21](=[O:23])[CH3:22])[C:17](O)=[O:18].N12CCN(CC1)CC2>ClCCl>[Br:15][C:16]1[C:17](=[O:18])[O:23][C:21](=[CH2:22])[C:20]=1[CH3:24]

Participants

5

Reactant 3

HCID 9237DabcoHCID 14812Phosphorus oxide (P4O10)HCID 9965725HCID 9965725, compound

Product 1

HCID 22287783HCID 22287783, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phosphorus pentoxide (11.5 g) was added with stirring to a solution of 2,3-dibromo-3-methyl-4-oxopentanoic acid (4.6 g, 16.0 mmol) in dry dichloromethane (30 ml). The mixture was heated at reflux with stirring for 2 h. It was cooled to room temperature and the resulting mixture was filtered through a pad of filter aid and treated with 1,4-diazabicyclo[2.2.2]octane (DABCO) (2.24 g, 14.8 mmol). The mixture was stirred at room temperature for 1 h, washed with dilute hydrochloric acid (2N, 10 ml), brine (20 ml), dried over sodium sulfate, and chromatographed on a short plug of silica gel to yield the 3-bromo-4-methyl-5-(methylene)-2(5H)furanone as a colourless oil (2.14 g, 83%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux
  3. filtrationthe resulting mixture was filtered through a pad of filter aid
  4. stirringThe mixture was stirred at room temperature for 1 h
  5. washwashed with dilute hydrochloric acid (2N, 10 ml), brine (20 ml)
  6. dry with materialdried over sodium sulfate
  7. customchromatographed on a short plug of silica gel

Sources & evidence

ORD record
ord-d0eb3f8dca4f452e92008477b17d216a
Source dataset
uspto-grants-2005_10
Patent number
US06958145B2

Reaction notes

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