Iodoethane → 2-Bromo-5-[(ethyloxy)methyl]furan

Temperature

0 °C

Sodium hydride (95%, 19 mg, 0.75 mmol) was diluted in dry DMF (0.5 mL) and cooled to 0° C. A solution of (5-bromo-2-furanyl)methanol (120 mg, 0.68 mmol) was added, and the mixture was stirred for 5 minutes. Ethyl iodide (117 mg, 0.75 mmol) was added, and the mixture was stirred at rt overnight. The reaction mixtures were quenched by the careful addition of water, then extracted with diethyl ether. The combined organics were dried and concentrated. The residue was purified by flash chromatography, eluting with 10% EtOAc/hexanes. The desired fractions were combined and concentrated to afford the title compound.

1. stirringthe mixture was stirred at rt overnight
2. customThe reaction mixtures
3. customwere quenched by the careful addition of water
4. extractionextracted with diethyl ether
5. customThe combined organics were dried
6. concentrationconcentrated
7. customThe residue was purified by flash chromatography
8. washeluting with 10% EtOAc/hexanes
9. concentrationconcentrated

ORD record

ord-f7df9f7d135a4c298f9e3806d15e1e6a

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071584B2