Hydrochloric Acid → HCID 90203531, compound

HRID 927032Notes

Reaction equation

HRID 927032 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[CH:13][CH:12]=2)=[N:8][O:9][CH:10]=1)=[O:5])C.[OH-].[Na+].Cl>C(O)C>[F:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][O:17][C:14]2[CH:13]=[CH:12][C:11]([C:7]3[C:6]([C:4]([OH:5])=[O:3])=[CH:10][O:9][N:8]=3)=[CH:16][CH:15]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90203318HCID 90203318, compound

Product 1

HCID 90203531HCID 90203531, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-[4-(4-fluoro-benzyloxy)-phenyl]-isoxazole-4-carboxylic acid ethyl ester (19.6 g, 57.5 mmol) in ethanol (65 mL) at 60° C. was treated with 2N aqueous NaOH (65 mL). After stirring for 14 h, the resulting yellow suspension was poured onto 500 mL of ice water and the mixture was adjusted to pH 2 with 4N HCl. The white suspension was removed by filtration and washed with water. The wet filter cake was dissolved in ethyl acetate and dried over Na2SO4. Filtration followed by removal of volatiles under reduced pressure gave crude material from which 3-[4-(4-fluoro-benzyloxy)-phenyl]-isoxazole-4-carboxylic acid (16.4 g, 91%) was isolated in pure form after washing twice with heptane, once with diethyl ether and dried in vacuo.

Workup

  1. customThe white suspension was removed by filtration
  2. washwashed with water
  3. dissolutionThe wet filter cake was dissolved in ethyl acetate
  4. dry with materialdried over Na2SO4
  5. filtrationFiltration
  6. customfollowed by removal of volatiles under reduced pressure

Sources & evidence

ORD record
ord-8d13b63ce09843af856f76a30495fb2f
Source dataset
uspto-grants-2016_03
Patent number
US09290465B2

Reaction notes

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