Diethyl Ether → Tetrahydro-1,4-oxazepine-4(5H)-acetonitrile

Temperature

70 °C

1,4-Oxazepane (292) (Turner, S. R. et al., PCT Int. Appl. WO 2000 040561, 2000) (4.95 g, 49.0 mmol) was added dropwise to a stirred aqueous solution of glycolonitrile (55%, 5.3 mL, 53.8 mmol) at 5° C. and stirred at 70° C. for 1 h. More aqueous glycolonitrile (55%, 0.96 mL, 6.13 mmol) was added and the mixture stirred for 30 min, cooled to 20° C. and Et2O (100 mL) and water (50 mL) were added. The aqueous layer was extracted with Et2O (4×30 mL), the combined organic fraction dried and the solvent evaporated to give nitrile 293 (3.24 g, 47%) as a pale yellow oil: 1H NMR δ 3.80-3.84 (m, 2H, H-5), 3.74-3.77 (m, 2H, H-3), 3.60 (s, 2H, CH2CN), 2.79-2.84 (m, 4H, H-2, H-7), 1.92-1.99 (m, 2H, H-6); HRMS calcd for C7H12N2O (M+) m/z 140.0950, found 140.0947.

1. stirringthe mixture stirred for 30 min
2. temperaturecooled to 20° C.
3. extractionThe aqueous layer was extracted with Et2O (4×30 mL)
4. customthe combined organic fraction dried
5. customthe solvent evaporated

ORD record

ord-0f9f8e14b0d644388c043bac253851a1

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989451B2