Chlorine monoxide → HCID 22930735, compound

HRID 1295256Notes

Reaction equation

HRID 1295256 reaction equation
O=[C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:4]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[O:3]1.O(Cl)[Cl:20]>N1C=CC=CC=1>[Cl:20][C:2]1[O:3][C:4]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1

Participants

4

Reactant 2

HCID 24646Chlorine monoxideHCID 69428138HCID 69428138, compound

Product 1

HCID 22930735HCID 22930735, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of methyl 3-(2-oxo-4-phenyloxazolin-5-yl)propionate (3.00 g), pyridine (0.98 ml) and phosphoric oxychloride (7.62 g) was stirred at 105° C. for 2 hrs. The reaction mixture was slowly poured into ice water and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was subjected to silica gel column chromatography, and methyl 3-(2-chloro-4-phenyl-5-oxazolyl)propionate (2.40 g, yield 75%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:7, volume ratio).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3f61688add4e467787d3bbf2db8c4029
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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