Dimethylformamide → HCID 86647905, compound

N,N-dimethylformamide (1.298 mL) in dichloromethane (2.0 mL) at −10° C. was treated dropwise with POCl3 (1.426 mL). The mixture was stirred for 5 minutes and then warmed to room temperature and stirred 30 minutes. The solution was cooled to −10° C., treated dropwise with a solution of 4-methoxy-4-methylcyclohexanone (1.74 g) in dichloromethane (2.5 mL) and stirred for 4 hours at ambient temperature. The reaction mixture was poured over a mixture of ice and 25% sodium acetate solution. When the ice had melted, the reaction mixture was poured into a reparatory funnel and extracted with diethyl ether (4×125 mL). The diethyl ether extracts were washed with aqueous NaHCO3 solution and brine, dried (MgSO4), filtered and concentrated. The concentrate was chromatographed on silica gel with 0 to 5% ethyl acetate in hexanes as the eluent.

1. stirringstirred 30 minutes
2. temperatureThe solution was cooled to −10° C.
3. stirringstirred for 4 hours at ambient temperature
4. additionthe reaction mixture was poured into a reparatory funnel
5. extractionextracted with diethyl ether (4×125 mL)
6. washThe diethyl ether extracts were washed with aqueous NaHCO3 solution and brine
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customThe concentrate was chromatographed on silica gel with 0 to 5% ethyl acetate in hexanes as the eluent

ORD record

ord-42acd7e1f61942919da41a033f90a067

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08586754B2