Triethylamine → HCID 67463574, compound

Temperature

4 °C

To a solution of (E)-acetaldehyde oxime (CAN 107-29-9, 1.0 g, 16.9 mmol), 2-methylbut-3-yn-2-amine (CAN 2978-58-7, 1.4 g, 16.9 mmol) and triethylamine (CAN 121-44-8, 0.17 g, 1.69 mmol) in methylene chloride (25 mL) at 0° C. was added a 5% aqueous solution of sodium hypochlorite (5%, 42.6 g) over 3 h. The reaction was allowed to warm to 4° C. and stirring continued for 5 h. The organic layer was separated, and the aqueous layer was extracted with methylene chloride (50 mL). The combined methylene chloride extracts were washed with saturated aqueous sodium chloride (60 mL) and dried over anhydrous magnesium sulfate. The solvent was removed to give a yellow oil. The crude product was purified by column chromatography (silica gel 30 g, eluting with 30% ethyl acetate in petroleum ether) to yield the product as yellow solid (0.1 g, 4.2%); MS (EI): m/e=141.2 [M+H]+.

1. customThe organic layer was separated
2. extractionthe aqueous layer was extracted with methylene chloride (50 mL)
3. washThe combined methylene chloride extracts were washed with saturated aqueous sodium chloride (60 mL)
4. dry with materialdried over anhydrous magnesium sulfate
5. customThe solvent was removed
6. customto give a yellow oil
7. customThe crude product was purified by column chromatography (silica gel 30 g, eluting with 30% ethyl acetate in petroleum ether)

ORD record

ord-8dd342a5f35c4336a61ce742c8aaea22

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290451B2