Methanol → 3-methyl-furan-2-carboxylic acid N'-isopropyl-hydrazide

A solution of methyl-3-methyl-2-furoate (250 mg, 1.78 mmol) and hydrazine monohydrate (1.8 ml, 34.68 mmol) in MeOH (3 ml) was heated to 120° C. for 20 minutes in a microwave oven. The mixture was concentrated to dryness and the residue was triturated with hexanes. The resulting hydrazide 1 was collected by suction filtration and air dried (242 mg). This material was dissolved in acetone (3 ml) and stirred at rt overnight. The solution was concentrated to dryness. The residue was dissolved in TFA (3 ml) and treated with triethylsilane (0.58 ml, 3.6 mmol) at rt overnight. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between saturated sodium bicarbonate and DCM. The organic layer was dried over sodium sulfate and concentrated under vacuum to afford the product as oil (268 mg, 82%).

1. concentrationThe mixture was concentrated to dryness
2. customthe residue was triturated with hexanes
3. filtrationThe resulting hydrazide 1 was collected by suction filtration and air
4. customdried (242 mg)
5. dissolutionThis material was dissolved in acetone (3 ml)
6. concentrationThe solution was concentrated to dryness
7. dissolutionThe residue was dissolved in TFA (3 ml)
8. concentrationThe reaction mixture was concentrated under reduced pressure
9. customthe residue was partitioned between saturated sodium bicarbonate and DCM
10. dry with materialThe organic layer was dried over sodium sulfate
11. concentrationconcentrated under vacuum

ORD record

ord-7e358d8d241a49cdb49ddf740cfdbf55

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07317125B2