Ethyl 3-(5-methyl-2-furanyl)propionate → 3-(5-Methyl-2-furanyl)-1-propanol

To a solution of ethyl 3-(5-methyl-2-furanyl)propionate (3.6 g, 20 mmol) in 50 mL of THF at 0° C. was added dropwise under nitrogen 8 mL of diisobutylaluminum hydride (1M in hexane), and the mixture was stirred at room temperature over-night. The resulting solution was diluted with 2 mL of water in 10 mL of THF and brine, and the mixture was stirred for 30 min. The solid was removed by filtration, and the filtrate was diluted with 20 mL of water, extracted with methylene chloride. The organic layer was washed with water, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by passing through MPLC column (ethyl acetate/hexane) to afford 1.11 g of the desired product.

1. stirringthe mixture was stirred for 30 min
2. customThe solid was removed by filtration
3. additionthe filtrate was diluted with 20 mL of water
4. extractionextracted with methylene chloride
5. washThe organic layer was washed with water
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated in vacuo
8. customThe residue was purified

ORD record

ord-bd29db187e044b57bff411fe76ece18f

Source dataset

uspto-grants-1996_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05514679