Sodium borohydride → HCID 57319589, compound

Temperature

0 °C

A solution of 5-vinyl-thiophene-2-carbaldehyde (900 mg, 6.4 mmol) in anhydrous methanol (20 mL) was cooled to 0° C. under an atmosphere of nitrogen and treated with sodium borohydride (268 mg, 7.1 mmol). The reaction was stirred at 0° C. for 5 minutes and then at room temperature for 5 minutes, before being quenched with water and concentrated in vacuo. The aqueous layer was extracted twice with dichloromethane, the combined organics dried through a hydrophobic frit and concentrated in vacuo. The product was purified by silica gel chromatography using iso-hexanes/ethyl acetate 7:1 then 2:1 to afford the title compound (800 mg, 88%) as a colourless oil. 1H NMR (300 MHz, CDCl3) δ1.76 (t, J=6.0 Hz, 1H), 4.80 (d, J=6.3 Hz, 2H), 5.15 (d, J=10.7 Hz, 1H), 5.55 (d, J=17.4 Hz, 1H), 6.78 (dd, J=17.4, 10.7 Hz, 1H), 6.85 (d, J=3.6 Hz, 1H), 6.88 (d, J=3.6 Hz, 1H).

1. waitat room temperature for 5 minutes
2. custombefore being quenched with water
3. concentrationconcentrated in vacuo
4. extractionThe aqueous layer was extracted twice with dichloromethane
5. customthe combined organics dried through a hydrophobic frit
6. concentrationconcentrated in vacuo
7. customThe product was purified by silica gel chromatography

ORD record

ord-395b21314b8547429fc856afbfdfb38d

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08933015B2