Chloromethyl Methyl Ether → HCID 68741732, compound

HRID 2242789Notes

Reaction equation

HRID 2242789 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH:13]([CH:16]1[CH2:21][CH2:20][O:19][C:17]1=[O:18])([CH3:15])[CH3:14].[CH3:22][O:23][CH2:24]Cl>C1COCC1>[CH:13]([C:16]1([CH2:22][O:23][CH3:24])[CH2:21][CH2:20][O:19][C:17]1=[O:18])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 7912DiisopropylamineHCID 13164942HCID 13164942, compoundHCID 178418339Butyllithium

Product 1

HCID 68741732HCID 68741732, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of diisopropylamine (13.1 mL) in THF was treated dropwise with butyl lithium (58.4 mL of 1.6M solution in hexanes) at −10° C. Then the reaction mixture was cooled to −70° C. and treated dropwise with 2-isopropyl-γ-butyrolactone (9.30 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 3 h at −70° C., then warmed-up to −40° C. and treated dropwise at this temperature with chloromethyl methyl ether (7.50 mL). After that, the mixture was allowed to slowly warm-up to room temperature and stirred at this temperature for 80 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 distilled in vacuum to give 7.00 g (57%) of the title compound.

Workup

  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 80 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. distillationdistilled in vacuum

Sources & evidence

ORD record
ord-8d3a08b3f2f34d248a897b1303283644
Source dataset
uspto-grants-2010_03
Patent number
US07674741B2

Reaction notes

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