Propargyl bromide → HCID 90010346, compound

Reaction equation

[H-].[Na+].[CH2:3]([O:10][CH2:11][C:12]([CH3:15])([OH:14])[CH3:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:17][C:18]#[CH:19]>C1COCC1>[CH3:13][C:12]([O:14][CH2:19][C:18]#[CH:17])([CH3:15])[CH2:11][O:10][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Procedure

To a mixture of NaH (5.0 g) in THF (50 mL) at 0° C. was added 1-(benzyloxy)-2-methylpropan-2-ol (9.36 g, 51.9 mmol) dropwise. After being stirred at room temperature for 0.5 h, 3-bromoprop-1-yne (12.4 g, 104 mmol) was added slowly at 0° C. The mixture was then stirred at reflux overnight. The reaction was quenched by addition of sat. NH4Cl. The resulting mixture was extracted with ethyl acetate (30 mL×3). The organic layer was combined, dried over with Na2SO4, and concentrated. The residue was purified by silica gel column chromatography eluting with petroleum ether/ethyl acetate (20/1) to afford the title compound (9.72 g, 86%) as pale yellow oil. 1H NMR (500 MHz, CDCl3) δ 7.34-7.35 (m, 5H), 4.56 (s, 2H), 4.18 (d, J=2.0 Hz, 2H), 3.38 (s, 2H), 2.34 (t, J=2.0 Hz, 1H), 1.25 (s, 6H).