Hexachloroethane → Methyl 2-chloro-1,3-oxazole-5-carboxylate

HRID 659746Notes

Reaction equation

HRID 659746 reaction equation
[CH3:1][O:2][C:3]([C:5]1[O:9][CH:8]=[N:7][CH:6]=1)=[O:4].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:20]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1.CCOC(C)=O.O>[CH3:1][O:2][C:3]([C:5]1[O:9][C:8]([Cl:20])=[N:7][CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 6214HexachloroethaneHCID 2724619Methyl 5-oxazolecarboxylateHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 26370182Methyl 2-chloro-1,3-oxazole-5-carboxylateYield 62%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22728543Water ethylacetateSolvent

Procedure

To a solution of oxazole-5-carboxylic acid methyl ester (1.4 g, 11 mmol) in anhydrous THF (50 mL) at −40° C. under an argon atmosphere was slowly added a solution of LiHMDS (13.3 mL, 1 M in THF). After 1 h at −40° C., solid hexachloroethane (3.91 g, 16.5 mmol) was added. The mixture was then allowed to slowly warm to room temperature and stir for 16 h. The reaction was diluted with AcOEt/H2O (30 mL/10 mL). The organic layer was washed with brine, dried with MgSO4 and filtered. After removal of solvent the residue was silica gel column chromatographed (CH2Cl2/Cyclohexane: 1/1) to give 1.1 g of 2-chloro-oxazole-5-carboxylic acid methyl ester (62%) as a white solid. m.p.=35-50° C.

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customAfter removal of solvent the residue
  5. customchromatographed (CH2Cl2/Cyclohexane: 1/1)

Sources & evidence

ORD record
ord-a10fd2556b40429a90762b6f539bffe1
Source dataset
uspto-grants-2011_12
Patent number
US08080669B2

Reaction notes

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