Hydrochloric Acid → HCID 57780765, compound

HRID 1668434Notes

Reaction equation

HRID 1668434 reaction equation
C([O-])([O-])=O.[Na+].[Na+].Cl[C:8]1[CH:12]=[CH:11][O:10][C:9]=1[C:13]1[CH:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16]([C:25]([O:27]C)=[O:26])(O)[O:15][N:14]=1.[ClH:29]>O.CO>[Cl:29][C:11]1[O:10][C:9]([C:13]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:16]([C:25]([OH:27])=[O:26])[O:15][N:14]=2)=[CH:8][CH:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 67345944HCID 67345944, compound

Product 1

HCID 57780765HCID 57780765, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of Na2CO3 (237 mg, 2.24 mmoles) in water (10 ml) was added to the methyl [3-(chlorofuran-2-yl)-4-phenyl-5-hydroxy-2-isoxazolin-5-yl]carboxylate (360 mg, 1.12 mmoles) in MeOH (10 ml). The reaction mixture was heated under reflux conditions for 2 h. It was then acidified with HCl and then the MeOH was distilled at a reduced pressure and CHCl3 was added. The two phases were separated and the aqueous phase was extracted three times with CHCl3. The combined organic phases were dried over anhydrous Na2SO4 and the solvent evaporated at a reduced pressure to give the crude [3-(5chlorofuran-2-yl)-4-phenylisoxazol-5-yl]carboxylic acid which is purified by crystallisation from CHCl3/hexane (300 mg, 93% yield). M.p. 168-170° C. FT-IR (KBr): 3500-2850, 1709, 1614, 1592, 1521, 1454, 1416, 1392, 1305, 1249, 1208, 1153, 1122, 1022, 1006, 981, 941, 899, 779, 696 cm−1. 1H NMR (300 MHz, CDCl3, δ): 7.48-7.42 (m, 3H, aromatic protons); 7.39-7.32 (m, 2H, aromatic protons); 7.00-6.50 (bs, 1H, OH: exchange with D2O); 6.14 (d, J=3.6 Hz, 1H, furyl proton); 6.12 (d, J=3.6Hz, 1H, furyl proton). 13C NMR (75 MHz, CDCl3, δ): 159.9, 154.8, 153.6, 141.6, 139.2, 129.4, 129.1, 128.3, 126.8, 123.9, 114.8, 107.9. LC-MS (ESI−): 288[(M−1)−, 69], 117 (100). Anal. Calc. for C14H8ClNO4: C, 58.05; H, 2.78; N, 4.83. Found: C, 58.07; H, 2.75; N, 4.80.

Workup

  1. temperatureThe reaction mixture was heated under reflux conditions for 2 h
  2. distillationthe MeOH was distilled at a reduced pressure and CHCl3
  3. additionwas added
  4. customThe two phases were separated
  5. extractionthe aqueous phase was extracted three times with CHCl3
  6. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  7. customthe solvent evaporated at a reduced pressure

Sources & evidence

ORD record
ord-3fcdfec21b2544e5846e200ccfc5d249
Source dataset
uspto-grants-2011_08
Patent number
US07989450B2

Reaction notes

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