Water → HCID 68153075, compound

HRID 2047248Notes

Reaction equation

HRID 2047248 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]([C:13]([O:15][CH3:16])=[O:14])[C:11](=O)[O:10][N:9]=2)=[CH:4][CH:3]=1.CCN(CC)CC.O.[OH-].[Na+].O=P(Cl)(Cl)[Cl:30]>>[Cl:30][C:11]1[O:10][N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:12]=1[C:13]([O:15][CH3:16])=[O:14]

Participants

6

Reactant 5

HCID 962WaterHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 68153087HCID 68153087, compound

Product 1

HCID 68153075HCID 68153075, compoundYield 57%

Conditions

Temperature
2.5 °C

Procedure

A suspension of methyl 3-(4-chlorophenyl)-5-oxo-4,5-dihydroisoxazole-4-carboxylate (518 mg, 2.04 mmol; building block is commercially available) in POCl3 (3 mL) was cooled to 0-5° C., and upon stirring, Et3N (0.3 mL) was added dropwise. The resulting mixture was heated to 100-110° C. and stirred at this temperature for 2-2.5 h, cooled to room temperature, poured into iced water and neutralized with aqueous NaOH (10%). The product was extracted with ether and purified by column chromatography (hexane:EtOAc 25:2) to give 320 mg of a yellow solid. Yield 57%. 1H NMR (DMSO-D6, CCl4): 3.79 (3H, s, OCH3), 7.50 (2H, AB-syst., CH-arom.), 7.65 (2H, AB-syst., CH-arom.).

Workup

  1. temperatureThe resulting mixture was heated to 100-110° C.
  2. stirringstirred at this temperature for 2-2.5 h
  3. temperaturecooled to room temperature
  4. extractionThe product was extracted with ether
  5. custompurified by column chromatography (hexane:EtOAc 25:2)

Sources & evidence

ORD record
ord-9b9d6f7ecee9404faa97527103e50150
Source dataset
uspto-grants-2013_11
Patent number
US08592456B2

Reaction notes

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