Hydrochloric Acid → 1-(3-Methyl-1,2-oxazol-5-yl)cyclopropane-1-carboxylic acid

HRID 931070Notes

Reaction equation

HRID 931070 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2([C:10]([O:12]C)=[O:11])[CH2:9][CH2:8]2)[O:4][N:3]=1.O.[OH-].[Li+].[Cl-].[NH4+].Cl>CO.O>[CH3:1][C:2]1[CH:6]=[C:5]([C:7]2([C:10]([OH:12])=[O:11])[CH2:8][CH2:9]2)[O:4][N:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 168937Lithium hydroxide, monohydrateHCID 89853625Methyl 1-(3-methylisoxazol-5-yl)cyclopropanecarboxylate

Product 1

HCID 825972691-(3-Methyl-1,2-oxazol-5-yl)cyclopropane-1-carboxylic acidYield 47%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To methyl 1-(3-methylisoxazol-5-yl)cyclopropanecarboxylate (100 mg, 0.552 mmol) was added a solution of lithium hydroxide monohydrate (32 mg, 0.76 mmol) in methanol (2 mL) and water (1 mL). The reaction mixture was stirred at room temperature for 18 h. The solvent was reduced to about 1 mL in volume. A saturated aqueous solution of ammonium chloride (2 mL) was added followed by aqueous hydrochloric acid (1N) until pH was approximately 4. The mixture was extracted with ether (15 mL×2). The combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford 1-(3-methylisoxazol-5-yl)cyclopropanecarboxylic acid as a white solid (43 mg, 47%). The material was used without further purification. MS (ES+) (M+H) 168.0; LCMS retention time: 2.0 minutes (Method L). 1H NMR (500 MHz, CD3OD) δ 1.44-1.48 (m, 2H), 1.66-1.69 (m, 2H), 2.25 (s, 3H), 6.38 (s, 1H).

Workup

  1. extractionThe mixture was extracted with ether (15 mL×2)
  2. dry with materialThe combined organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7d0049ba8d49423180b7c001dfffb3a6
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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