Dimethylformamide → HCID 86647905, compound

Dimethylformamide (1.298 mL) in dichloromethane (2.0 mL) at −10° C. was treated dropwise with POCl3 (1.426 mL) to give a colorless solution. The mixture was stirred 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% aqueous sodium acetate solution. After the ice melted, the reaction mixture was poured into a separatory funnel and extracted with diethyl ether (4×125 mL). The diethyl ether extracts were washed with 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. customto give a colorless solution
2. stirringstirred 30 minutes
3. temperatureThe solution was cooled to −10° C.
4. stirringstirred for 4 hours at ambient temperature
5. additionthe reaction mixture was poured into a separatory funnel
6. extractionextracted with diethyl ether (4×125 mL)
7. washThe diethyl ether extracts were washed with NaHCO3 solution and brine
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customThe concentrate was chromatographed on silica gel with 0 to 5% ethyl acetate in hexanes as the eluent

ORD record

ord-e9dd95c2b59344d18eafce7c83233ec8

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08580794B2