Propargyl bromide → HCID 57887514, compound

To a 60% suspension of sodium hydride in mineral oil (2.3 g, 57.6 mmol) in tetrahydrofuran (65 mL) was added 2-isopropoxyethanol (3.0 g, 28.8 mmol) dropwise at about 0 C. The mixture was stirred for about 30 min, then propargyl bromide (3.2 mL, 28.8 mmol) was added dropwise and the mixture was stirred overnight while being allowed to warm to room temperature. The reaction was quenched by addition of water and the product was extracted with diethyl ether. The combined organic extracts were dried (MgSO4), filtered and the organic solvents were carefully distilled off at atmospheric pressure. The residue was purified by flash chromatography on silica gel using diethyl ether/n-pentane (1:6) as eluent to provide Example 613. 1H NMR (500 MHz, CDCl3): δ 1.17 (d, J=6.0 Hz, 6H), 2.42 (t, J=3.0 Hz, 1H), 3.57-3.76 (m, 5H), 4.21 (d, J=3.0 Hz, 2H).

1. stirringthe mixture was stirred overnight
2. customThe reaction was quenched by addition of water
3. extractionthe product was extracted with diethyl ether
4. dry with materialThe combined organic extracts were dried (MgSO4)
5. filtrationfiltered
6. distillationthe organic solvents were carefully distilled off at atmospheric pressure
7. customThe residue was purified by flash chromatography on silica gel
8. customto provide Example 613

ORD record

ord-45b8d5c97bc047c0a4102adeb37d910c

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07468371B2