Water → Ethyl 5-chloro-1,2-oxazole-3-carboxylate

HRID 1918506Notes

Reaction equation

HRID 1918506 reaction equation
C(N([CH2:6][CH3:7])CC)C.Cl[C:9](=[N:15][OH:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11].O.[Cl:18]CCl>ClC(Cl)=C>[Cl:18][C:6]1[O:16][N:15]=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 8471TriethylamineHCID 6816376Ethyl chloro(hydroximino)acetate

Product 1

HCID 66831968Ethyl 5-chloro-1,2-oxazole-3-carboxylateYield 39%

Reagents, catalysts & solvents 1

HCID 6366Vinylidene chlorideSolvent2×

Procedure

A mixture of triethylamine (13.12 mL; 90.73 mmol) in 1,1-dichloroethene (75 mL) was added to ethyl 2-chloro-2-(hydroxyimino)acetate (5.5 g; 36.29 mmol) in 1,1-dichloroethene (50 mL) over a period of 2 h the reaction mixture was stirred at room temperature for 20 min and portioned between water (75 mL) and dichloromethane (75 mL). The aqueous were extracted with dichloromethane, the organic layers rejoined were dried, concentrated under reduced pressure and the crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to afford ethyl 5-chloroisoxazole-3-carboxylate 2.5 g (39%).

Workup

  1. extractionThe aqueous were extracted with dichloromethane
  2. customthe organic layers rejoined were dried
  3. concentrationconcentrated under reduced pressure
  4. customthe crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-197f0c4b09bf416b96cc63fec99fd362
Source dataset
uspto-grants-2013_12
Patent number
US08618138B2

Reaction notes

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