Allyl bromide → HCID 86622345, compound

Participants

Reaction Steps

Step AK (2): (R)-2,2,2-trifluoro-N-(1-hydroxy-4-methylpentan-2-yl)-acetamide (200 mg, 0.94 mmol) was dissolved in THF (5 mL) under nitrogen atmosphere. Sodium hydride (80 mg, 1.9 mmol) was added to the reaction mixture in portions. 3-Bromoprop-1-ene (0.16 mL, 1.9 mmol) was added dropwise to the reaction mixture. The reaction mixture was stirred at rt for 3 h and was extracted with EtOAc. The combined organic phases were washed with water and brine and dried over Na2SO4, filtered and concentrated in vacuum. The residue was purified by silica gel chromatography to give (R)-N-(1-(allyloxy)-4-methylpentan-2-yl)-2,2,2-trifluoroacetamide (210 mg, 88%) as a colorless oil. LC-MS (M+H)+=254.06. 1H NMR (CD3OD, 500 MHz) δ 5.91 (m, 1H) 5.31-5.17 (m, 2H) 4.21 (m, 1H) 4.05-3.97 (m, 2H) 3.49-3.42 (m, 2H) 1.63 (m, 1H) 1.52 (m, 1H) 1.39 (m, 1H) 0.97-0.93 (m, 6H).

Provenance & Evidence