Triphenylphosphine → HCID 118098695, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of triphenylphosphine (355 mg, 1.354 mmol) in THF (4 mL) at 0° C., was added DIAD (0.263 mL, 1.354 mmol) dropwise. The mixture was stirred at 0° C. for 10 min affording a colorless suspension. A solution of 6B (300 mg, 0.903 mmol) and (R)-1-methoxypropan-2-ol (0.133 mL, 1.354 mmol) in THF (2 mL) was added dropwise. The resultant dark red solution was stirred at 0° C. for 0.5 h, then was allowed to slowly warm to rt over night. The reaction mixture was concentrated. The crude product was purified by flash chromatography (loaded in chloroform onto a 40 g column and eluted with a gradient from 0 to 40% ethyl acetate/hexanes) to afford 6C (396 mg, 108% yield) as yellow oil/semi-solid. MS (ESI) m/z: 405.2 [M+1]+; 1H NMR (400 MHz, chloroform-d) δ ppm 8.07 (d, J=8.53 Hz, 1H) 7.96 (d, J=18.57 Hz, 1H) 7.32-7.51 (m, 6H) 5.11-5.26 (m, 2H) 4.59 (d, J=18.07 Hz, 2H) 3.58-3.68 (m, 1H) 3.47 (d, J=6.53 Hz, 2H) 3.37 (s, 3H) 2.99 (br. s., 3H) 1.40 (br. s., 3H).

Provenance & Evidence