Chloroform → HCID 10560186, compound

Temperature

0 °C

To a stirred solution of 4-methoxy-2,6-bis(hydroxymethyl)pyridine (2.89 g, 17.10 mmol)-and triethylamine (9.6 ml, 68.40 mmol) at 0° C. in 100 ml of anhydrous dichloromethane and 50 ml of chloroform under an argon atmosphere was added methanesulphonyl chloride (3.9 ml, 51.30 mmol). The solution was stirred at 0° C. for 30 minutes, warmed to room temperature and stirred a further 24 hours. Additional methanesulphonyl chloride (1.5 ml, 19.38 mmol) was added and the mixture was stirred at 50° C. for 24 hours. The reaction mixture was quenched with H2O (50 ml), the aqueous phase extracted with CH2Cl2, dried over MgSO4 and concentrated to afford an orange oil. The residual oil was passed through a short plug of silica gel using dichloromethane as eluent thus affording after concentration a pale yellow solid which was identified by 1H NMR as 4-methoxy-2,6-bis-(chloromethyl)pyridine (2.3 g, 66%).

1. temperaturewarmed to room temperature
2. stirringstirred a further 24 hours
3. stirringthe mixture was stirred at 50° C. for 24 hours
4. customThe reaction mixture was quenched with H2O (50 ml)
5. extractionthe aqueous phase extracted with CH2Cl2
6. dry with materialdried over MgSO4
7. concentrationconcentrated
8. customto afford an orange oil
9. customthus affording
10. concentrationafter concentration a pale yellow solid which

ORD record

ord-9c1a34ab500c444ca087da8780206a5a

Source dataset

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05698546