Allyl bromide → HCID 10388413, compound

Participants

Reaction Conditions

Reaction Steps

Tert-Butyl(dimethyl)[2,2,2-trifluoro-1-{4-[(phenylsulfonyl)methyl]phenyl}-1-(trifluoromethyl)ethoxy]silane (378 mg, 0.74 mmol) was dissolved in anhydrous THF (10 mL) under argon and cooled to −78° C. 1.6M BuLi solution in hexanes (0.5 mL, 0.85 mmol) was added and the reaction was allowed to warm to 0° C. After 30 min at 0° C., the reaction was cooled to −78° C. and DMPU (0.26 mL, 2.1 mmol) was added, followed by allyl bromide (0.07 mL, 0.81 mmol). The reaction was allowed to warm to 0° C. and monitored by thin layer chromatography. The reaction was quenched with saturated NH4Cl and diluted with ethyl acetate. The layers were separated and the organic phase was washed with brine, dried (MgSO4), and concentrated in vacuo. Purification by flash chromatography (6:1 hexanes/EtOAc) afforded the protected sulfone as a colorless oil. The sulfone was deprotected as described in Example 2 step 3. Purification by flash chromatography (6:1 hexanes/EtOAc) afforded the title compound as a white solid (266 mg, 82%): mp=148° C. 1H NMR (CDCl3) δ 7.55 (m, 3H), 7.45 (d, 2H), 7.33 (t, 2H), 7.17 (d, 2H), 5.55 (m, 1H), 5.04 (m, 2H), 4.14 (dd, 1H), 3.51 (br s, 1H), 3.21 (m, 1H), 2.93 (m, 1H). Anal. Calc. for C19H16O3SF6: C, 52.06; H, 3.68. Found: 52.04; H, 3.45. HRMS (M+NH4+) Calc.: 456.1068. Found: 456.1075.

Provenance & Evidence