Methanol → 4-Methyl-5-vinylisoxazole-3-carboxylic acid

Ethyl 4-methyl-5-vinylisoxazole-3-carboxylate (250 mg, 0.993 mmol) was dissolved in THF (5.3 mL) and MeOH (3.2 mL) and to this was added 2M NaOH (aq) (497 μl, 0.993 mmol). The reaction mixture was stirred at room temperature for 15 minutes. The resulting mixture was concentrated under reduced pressure and treated with 2M HCl (5 mL) and water (5 mL). DCM was added to the aqueous resulting in the formation of an emulsion. The solvent was removed under reduced pressure. The resulting residue was suspended in DCM (25 mL) and passed through a phase separating column. The organic solvent was removed under reduced pressure to afford the title compound;

1. concentrationThe resulting mixture was concentrated under reduced pressure
2. additiontreated with 2M HCl (5 mL) and water (5 mL)
3. additionDCM was added to the
4. customaqueous resulting in the formation of an emulsion
5. customThe solvent was removed under reduced pressure
6. customseparating column
7. customThe organic solvent was removed under reduced pressure

ORD record

ord-6764513a22664d4bbe29f3682271e318

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403810B2