Water → 3-Propyl-1,2-benzisoxazole-5-carboxylic acid

HRID 14251Notes

Reaction equation

HRID 14251 reaction equation
[CH2:1]([C:4]1[C:8]2[CH:9]=[C:10]([C:13]([O:15]C)=[O:14])[CH:11]=[CH:12][C:7]=2[O:6][N:5]=1)[CH2:2][CH3:3].O1CCCC1.O.[OH-].[Li+]>CO>[CH2:1]([C:4]1[C:8]2[CH:9]=[C:10]([C:13]([OH:15])=[O:14])[CH:11]=[CH:12][C:7]=2[O:6][N:5]=1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 21086192Methyl 3-propyl-1,2-benzisoxazole-5-carboxylate

Product 1

HCID 210858433-Propyl-1,2-benzisoxazole-5-carboxylic acidYield 88.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-propyl-1,2-benzisoxazole-5-carboxylate (90 mg, 0.4 mmol) in a 2:1:1 mixture of tetrahydrofuran, water, and methanol (4 mL) was added lithium hydroxide (50 mg, 1.2 mmol) and the resulting reaction mixture stirred at room temperature for 2.5 h. The reaction mixture was concentrated under reduced pressure, and partitioned between water and ethyl ether. The aqueous layer was washed twice with ether and acidified to pH 1 with 6 M hydrochloric acid. The resulting aqueous layer was extracted with ethyl acetate, dried (sodium sulfate), and concentrated under reduced pressure to afford 3-propyl-1,2-benzisoxazole-5-carboxylic acid (73 mg): 1H NMR (300 MHz, CD3OD): δ 8.28-8.27 (m, 1H), 8.09-8.06 (m, 1H), 7.64-7.61 (m, 1H), 2.99-2.94 (m, 2H), 1.96-1.86 (m, 2H), 1.08-1.02 (m, 3H).

Workup

  1. customthe resulting reaction mixture
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompartitioned between water and ethyl ether
  4. washThe aqueous layer was washed twice with ether
  5. extractionThe resulting aqueous layer was extracted with ethyl acetate
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f27401906f204686bbcdb2c62a5e0eae
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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