Hydrochloric Acid → 5-[5-(2-Hydroxy-phenyl)-isoxazol-3-yl]-pentanoic acid

HRID 1039211Notes

Reaction equation

HRID 1039211 reaction equation
O[Li].O.C([O:6][C:7](=[O:24])[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[OH:23])[O:14][N:13]=1)C.Cl>O.O1CCOCC1>[OH:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:15]1[O:14][N:13]=[C:12]([CH2:11][CH2:10][CH2:9][CH2:8][C:7]([OH:24])=[O:6])[CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 1362065315-[5-(2-Hydroxy-phenyl)-isoxazol-3-yl]-pentanoic acid ethyl ester

Product 1

HCID 1364006025-[5-(2-Hydroxy-phenyl)-isoxazol-3-yl]-pentanoic acidYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Add a solution of LiOH.H2O (2.87 g, 68.4 mmol) in water (60 mL) to a rapidly stirred solution of 5-[5-(2-hydroxy-phenyl)-isoxazol-3-yl]-pentanoic acid ethyl ester (3.96 g, 13.7 mmol) in dioxane (120 mL) and stir at room temperature overnight. After 1 hour, acidify to pH 1 with 5N HCl solution and concentrate to remove the majority of the dioxane. Add water to residue and place in refrigerator overnight. Filter out solids, wash with water, dry in a 50° C. vacuum oven for 6 hours to afford the title compound (3.11 g, 87%). MS (IS) 262 (M+1)+.

Workup

  1. waitAfter 1 hour
  2. concentrationconcentrate
  3. customto remove the majority of the dioxane
  4. customplace in refrigerator overnight
  5. filtrationFilter out solids
  6. washwash with water
  7. customdry in a 50° C. vacuum oven for 6 hours

Sources & evidence

ORD record
ord-9c2bdb2ca52b4516bde76a4a3ea02c4c
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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