Triethylamine → (E)-5-(2-cyclohexylvinyl)furan-2-carbaldehyde

A mixture of 5-bromofuran-2-carbaldehyde (1.03 g, 5.89 mmol), vinylcyclohexane (0.86 g, 7.80 mmol), P(o-Tol)3 (0.089 g, 0.29 mmol), Pd(OAc)2 (0.070 g, 0.31 mmol) and Et3N (2.0 mL) in anhydrous DMF (3.0 mL) was degassed by bubbling Ar then alternating vacuum/Ar three times. The reaction mixture was heated under inert atmosphere at +90° C. for 20 hrs and cooled to room temperature. Aqueous NH4Cl was added to the reaction mixture and the mixture was extracted twice with hexanes and EtOAc. Combined organic layers were washed with brine, concentrated under reduced pressure. Purification by flash chromatography (3%-8% EtOAc—hexanes gradient) gave (E)-5-(2-cyclohexylvinyl)furan-2-carbaldehyde as a yellow oil. Yield (0.40 g, 33%); 1H NMR (400 MHz, CDCl3) δ 9.53 (s, 1H), 7.19 (d, J=3.8 Hz, 1H), 6.55 (dd, J=7.0, 16.1 Hz, 1H), 6.34 (d, J=3.5 Hz, 1H), 6.19-6.26 (m, 1H), 2.10-2.19 (m, 1H), 1.52-1.92 (m, 6H), 1.10-1.42 (m, 4H).

1. customwas degassed
2. customby bubbling Ar
3. temperatureThe reaction mixture was heated under inert atmosphere at +90° C. for 20 hrs
4. additionAqueous NH4Cl was added to the reaction mixture
5. extractionthe mixture was extracted twice with hexanes and EtOAc
6. washCombined organic layers were washed with brine
7. concentrationconcentrated under reduced pressure
8. customPurification by flash chromatography (3%-8% EtOAc—hexanes gradient)

ORD record

ord-df99f471ba0644c9ac6d385deca2f23d

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09447078B2