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

Temperature

-78 °C

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

1. customreaction mixture
2. temperaturewarmed to 0° C. for 5 mins
3. temperaturecooled back down to −78° C
4. waitthe reaction mixture was kept at −78° C. for another 10 mins before it
5. temperatureto warm to room temperature overnight
6. customThe reaction mixture was quenched with aqueous ammonium chloride, and volatile solvents
7. customwere removed under reduced pressure
8. extractionThe product was extracted from water with ether
9. concentrationconcentrated
10. customThe crude oil was purified on biotage SP1, on column 65i

ORD record

ord-742f9fb203d54bb584e8144f086056c3

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394858B2