Sodium hydride → HCID 64005706, compound

Temperature

0 °C

To a stirred solution of 1,3-propanesultam (2.000 g, 16.5 mmol) in anhydrous N,N-dimethylformamide (30 mL) at 0° C. was added 60% sodium hydride in mineral oil (1.981 g, 49.5 mmol) and the mixture was stirred at 0° C. for 1 hr. 3-Chloro-3-methyl-1-butyne (2.300 g, 22.4 mmol) was added and the reaction mixture was stirred at 0° C. for 1 hr and then slowly warmed to room temperature and stirred for 16 hrs. The reaction was carefully quenched with water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), and concentrated in vacuo. The residue was purified by silica gel chromatography (0-70% ethyl acetate/hexanes) to afford the desired product as a yellow oil (1.35 g, 44%). 1H NMR (300 MHz, CDCl3) δ 3.52 (t, 2H, J=6.6 Hz), 3.23 (t, 2H, J=7.5 Hz), 2.46 (s, 1H), 2.42-2.28 (m, 2H), 1.74 (s, 6H).

1. stirringthe reaction mixture was stirred at 0° C. for 1 hr
2. temperatureslowly warmed to room temperature
3. stirringstirred for 16 hrs
4. customThe reaction was carefully quenched with water
5. extractionextracted with ethyl acetate
6. washThe organic layer was washed with saturated aqueous sodium chloride
7. dry with materialdried (anhydrous sodium sulfate)
8. concentrationconcentrated in vacuo
9. customThe residue was purified by silica gel chromatography (0-70% ethyl acetate/hexanes)

ORD record

ord-011a53df4f2b458a827379c2560733dd

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09265772B2