Allyl bromide → Ethyl 1-allyl-4-(tert-butyldimethylsilyloxy)cyclohexanecarboxylate

Participants

Reaction Conditions

Reaction Steps

4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexanecarboxylic acid ethyl ester (5.3 g, 18.50 mmol) in THF (56 ml) was cooled to −78° C. and then potassium hexamethyldisilazide (KHMDS) (74.0 ml, 37.0 mmol) (0.5M in toluene) was added slowly and reaction mixture was stirred at −78° C. for 10 min., then warmed to 0° C. for 5 mins and cooled back down to −78° C. 3-Bromo-propene (2.401 ml, 27.8 mmol) was added via syringe, and the reaction mixture was kept at −78° C. for another 10 mins before it was allowed to warm to room temperature overnight. The reaction mixture was quenched with aqueous ammonium chloride, and volatile solvents were removed under reduced pressure. The product was extracted from water with ether and concentrated. The crude oil was purified on biotage SP1, on column 65i, using gradient 5-35% EtOAc in heptane, with 25×150 tubes. Since the product as not UV active, it was detected by iodine staining. The product was a clear oil (4.88 g, 71%). LCMS [M+H]=327.2

Provenance & Evidence