Ethanol → HCID 66745792, compound

To a solution of (E)-2-(4-methoxybut-2-enyloxy)-6-nitrobenzonitrile (Example 184c) (0.25 g, 1.00 mmol) in a mixture of AcOH, EtOH and water (33 mL, 1:1:1) was added iron powder (0.56 g, 10.00 mmol) at rt. The obtained mixture was stirred at rt for 20 min, then was heated to 50° C. for a further 15 min, and allowed to cool. The suspension was concentrated under reduced pressure; the residue was treated with water (50 mL) and extracted with EtOAc (4×50 mL). The combined extract was washed with saturated aqueous NaHCO3 and brine, and was dried over anhydrous MgSO4. The filtrate was evaporated and the residue was purified by silica gel flash chromatography using gradient hexanes→hexanes/EtOAc (1:1), to give 0.19 g (86%) of the title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ 7.17 (t, J=8.4 Hz, 1H), 6.34 (d, J=8.8 Hz, 1H), 6.22 (d, J=8.4 Hz, 1H), 6.00 (broad s, 2H), 5.82-5.96 (m, 2H), 4.56-4.62 (m, 2H), 3.88-3.93 (m, 2H), 3.23 (s, 3H).

1. temperaturewas heated to 50° C. for a further 15 min
2. temperatureto cool
3. concentrationThe suspension was concentrated under reduced pressure
4. additionthe residue was treated with water (50 mL)
5. extractionextracted with EtOAc (4×50 mL)
6. extractionThe combined extract
7. washwas washed with saturated aqueous NaHCO3 and brine
8. dry with materialwas dried over anhydrous MgSO4
9. customThe filtrate was evaporated
10. customthe residue was purified by silica gel flash chromatography

ORD record

ord-4aa9c3ea8ac2490897149254a8884950

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09000054B2