Dimethyl Sulfoxide → HCID 86662315, compound

Temperature

-78 °C

An oven dried flask (50 ml, round bottom) containing dry dichloromethane (13 ml) is cooled to −78° C. (dry ice/acetone bath) under argon atmosphere. Oxalyl chloride (0.23 ml, 2.67 mmol) is added followed by the addition of dry dimethyl sulfoxide (0.31 ml, 4.31 mmol) via drop-wise addition. The mixture is stirred for 10 minutes and then a solution of 2-(6-chloropyridin-3-yloxy)-2-methylpropan-1-ol (451 mg, 2.06 mmol) [dissolved in dichloromethane (4 ml)] is added via slow drop-wise addition. The cooled solution was stirred for 30 minutes and then triethylamine (1.15 ml, 8.2 mmol) was added and the cooling bath was removed. The mixture was stirred and warmed to ambient over 1 hour. A saturated solution of sodium bicarbonate (20 ml) was added and also dichloromethane (20 ml). The material was transferred and shaken in a reparatory funnel. The dichloromethane phase was collected and washed with brine solution (25 mL). The aqueous phase was back extracted with methylene chloride (2×20 mL) and the organic phases combined, dried over magnesium sulfate, filtered and stripped. The material was purified by filtration through a short column of silica gel (20 g), eluting with 30% ethyl acetate/hexanes, which provided the product as a light yellow oil (361 mg). (M+H)+=200 m/e.

1. customAn oven dried flask (50 ml, round bottom)
2. additioncontaining dry dichloromethane (13 ml)
3. stirringThe cooled solution was stirred for 30 minutes
4. customthe cooling bath was removed
5. stirringThe mixture was stirred
6. temperaturewarmed
7. waitto ambient over 1 hour
8. additionA saturated solution of sodium bicarbonate (20 ml) was added
9. stirringshaken in a reparatory funnel
10. customThe dichloromethane phase was collected
11. washwashed with brine solution (25 mL)
12. extractionThe aqueous phase was back extracted with methylene chloride (2×20 mL)
13. dry with materialdried over magnesium sulfate
14. filtrationfiltered
15. filtrationThe material was purified by filtration through a short column of silica gel (20 g)
16. washeluting with 30% ethyl acetate/hexanes, which

ORD record

ord-14ab894d20d34e368b57777158a73239

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08940741B2