Chloromethyl Methyl Ether → HCID 68741659, compound

HRID 2242792Notes

Reaction equation

HRID 2242792 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[C:13]1([CH:19]2[CH2:24][CH2:23][O:22][C:20]2=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:25][O:26][CH2:27]Cl>C1COCC1>[C:13]1([C:19]2([CH2:25][O:26][CH3:27])[CH2:24][CH2:23][O:22][C:20]2=[O:21])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 7912DiisopropylamineHCID 232693-Phenyloxolan-2-oneHCID 178418339Butyllithium

Product 1

HCID 68741659HCID 68741659, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-90 °C

Procedure

Butyl lithium (62.5 mL of 1.6M solution in hexanes) was treated dropwise with a solution of diisopropylamine (14.0 mL) in THF (200 mL) at −20° C. and the resulted mixture was stirred for additional 30 min at the same temperature. After that the mixture was cooled to −90° C., treated dropwise with a solution of 2-phenyl-γ-butyrolactone (11.0 g) in THF (50 mL) and then stirred for 45 min at the same temperature. Next the reaction mixture was treated dropwise with a solution of chloromethyl methyl ether (8.05 g) in THF (50 mL), stirred for additional 10 min, then allowed to slowly warm-up to room temperature and stirred at this temperature for 16 h. Subsequently the reaction mixture was quenched by pouring onto a mixture of ice and 10% aqueous phosphoric acid. The formed organic phase was separated and the aqueous phase was extracted with chloroform. The combined organic phases were washed with saturated aqueous solution of potassium bicarbonate, then water, dried over magnesium sulfate, filtered, concentrated on a rotary evaporator and distilled in vacuum to give 11.5 g (82%) of the title compound.

Workup

  1. stirringstirred for 45 min at the same temperature
  2. stirringstirred for additional 10 min
  3. temperatureto slowly warm-up to room temperature
  4. stirringstirred at this temperature for 16 h
  5. customSubsequently the reaction mixture was quenched
  6. additionby pouring onto a mixture of ice and 10% aqueous phosphoric acid
  7. customThe formed organic phase was separated
  8. extractionthe aqueous phase was extracted with chloroform
  9. washThe combined organic phases were washed with saturated aqueous solution of potassium bicarbonate
  10. dry with materialwater, dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated on a rotary evaporator
  13. distillationdistilled in vacuum

Sources & evidence

ORD record
ord-c5faa25b04ac418a931cb9366716863b
Source dataset
uspto-grants-2010_03
Patent number
US07674741B2

Reaction notes

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