Chloromethyl Methyl Ether → HCID 68744172, compound

Temperature

-78 °C

A solution of diisopropylamine (19.0 mL) in THF was treated dropwise with butyl lithium (82.5 mL of 1.6M solution in hexanes) at −10° C. Next the reaction mixture was cooled to −78° C. and treated dropwise with 2-(cyclohexyl-methyl)-γ-butyrolactone (18.0 mL) keeping the speed of the addition at such a rate that the temperature of the mixture remained below −60° C. After completion of the addition, the mixture was stirred for 4.5 h at −78° C., then warmed-up to −40° C. and treated dropwise at this temperature with chloromethyl methyl ether (10.8 mL). After that, the mixture was allowed to slowly warm-up to room temperature and stirred at this temperature for 60 h. The solvents were removed in vacuum and the residue was redissolved in dichloromethane, then washed with a saturated aqueous solution of ammonium chloride, dried over magnesium sulfate, filtered, concentrated on a rotary evaporator and finally distilled in vacuum to give 5.90 g (25%) of the title compound.

1. additionthe speed of the addition at such a rate that the temperature of the mixture
2. customremained below −60° C
3. additionAfter completion of the addition
4. temperaturewarmed-up to −40° C.
5. temperatureto slowly warm-up to room temperature
6. stirringstirred at this temperature for 60 h
7. customThe solvents were removed in vacuum
8. dissolutionthe residue was redissolved in dichloromethane
9. washwashed with a saturated aqueous solution of ammonium chloride
10. dry with materialdried over magnesium sulfate
11. filtrationfiltered
12. concentrationconcentrated on a rotary evaporator
13. distillationfinally distilled in vacuum

ORD record

ord-113a69e762464d94a13f3acfd5d7046b

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07674741B2