Acetonitrile → HCID 86694640, compound

Temperature

0 °C

Anhydrous CH3CN (0.15 mL, 2.87 mmol) was added to a solution of LiHMDS (1M/THF, 3.0 mL, 3.0 mmol) at −75° C. under inert atmosphere and the reaction mixture was stirred for 5 min. A solution of methyl 5-((2-propylpentyl)oxy)furan-2-carboxylate (1.337 mmol) in anhydrous THF (7 mL) was added to the reaction mixture and the reaction mixture was stirred under inert atmosphere while slowly warming to 0° C. for over 75 min. The reaction mixture was partitioned between aqueous NaHSO4 (10%) and EtOAc. Organic layer was washed with brine, concentrated under reduced pressure. Flash chromatography purification (10%-50% EtOAc—hexanes gradient) gave 3-oxo-3-(5-((2-propylpentyl)oxy)furan-2-yl)propanenitrile as an off-white solid. Yield (0.23 g, 66%); 1H NMR (400 MHz, DMSO-d6) δ 7.57 (d, J=3.8 Hz, 1H), 5.78 (d, J=3.8 Hz, 1H), 4.30 (s, 2H), 4.08 (d, J=5.6 Hz, 2H), 1.69-1.79 (m, 1H), 1.23-1.35 (m, 8H), 0.80-0.88 (m, 6H).

1. stirringthe reaction mixture was stirred under inert atmosphere
2. customThe reaction mixture was partitioned between aqueous NaHSO4 (10%) and EtOAc
3. washOrganic layer was washed with brine
4. concentrationconcentrated under reduced pressure
5. customFlash chromatography purification (10%-50% EtOAc—hexanes gradient)

ORD record

ord-cd40dc569aea40ba9e45d2a31b9c0ad1

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09447078B2