Acetonitrile, 2,2-diethoxy- → Methyl 2,2-diethoxyethanecarboximidate

To a solution of sodium methoxide (13.38 g, 248 mmol) in MeOH (300 mL) was added dropwise 2,2-diethoxyacetonitrile (17.22 mL, 124 mmol). The resulting mixture was stirred at rt for 16 h. The reaction was then diluted with 300 mL of water and the product was extracted with 3×250 mL of Et2O. The combined Et2O layers were washed with 100 mL of brine, dried over sodium sulfate, and evaporated to give the desired product as a colorless liquid (15.3 g, 95 mmol, 77% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.86 (1H, br. s.), 4.77 (1H, s), 3.78 (3H, s), 3.55 (4H, qd, J=6.97, 4.28 Hz), 1.21 (7H, t, J=7.05 Hz).

1. extractionthe product was extracted with 3×250 mL of Et2O
2. washThe combined Et2O layers were washed with 100 mL of brine
3. dry with materialdried over sodium sulfate
4. customevaporated

ORD record

ord-4defcff09bf04d74a0607bdc46640930

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08309577B2