Dimethyl Sulfoxide → HCID 86662315, compound

Participants

Reaction Conditions

Reaction Steps

An oven dried flask containing 350 ml dry CH2Cl2 was cooled to −78° C. under argon. The oxalyl chloride (31.0 g, 20.7 mL, 244 mmol, Eq: 1.30) was added followed by the addition of DMSO (28 mL, 394 mmol, 2.1 equiv) via dropwise addition. The mixture is stirred for 10 minutes and then a solution of 2-(6-chloropyridin-3-yloxy)-2-methylpropan-1-ol (41.17 g of 92% pure material, 188 mmol, Eq: 1.00), dissolved in 60 ml CH2Cl2, was added via slow dropwise addition. The mixture is stirred for 30 minutes at −78° C. Triethylamine (105 mL, 751 mmol, 4 equiv) was added and the cooling bath was removed and the reaction mixture was allowed to stir for 1 hour with warming to ambient temperature. The reaction mixture was diluted with saturated NaHCO3 (275 mL), shaken and the organic phase collected and washed with an equal volume of brine. The aqueous phase was back-extracted with DCM (2×150 ml). The combined organics phase was dried (MgSO4), filtered and concentrated in vacuo. This resulting residue was purified by Analogix MPLC (SF40-240G column) eluting with 2% to 30% EtOAC/Hex gradient over 60 minutes to afford the desired product (37.1 g) as a light yellow oil. (M+H)+=200 m/e. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.44 (s, 6 H) 7.07-7.34 (m, 2 H) 8.05 (d, J=3.02 Hz, 1 H) 9.79 (s, 1 H).

Provenance & Evidence