Chloromethyl Methyl Ether → HCID 22319851, compound

HRID 498112Notes

Reaction equation

HRID 498112 reaction equation
[C:1]1([CH:7]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12](=[O:17])[CH:11]=[CH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(NC(C)C)(C)C.ClCOC>ClCCl>[C:1]1([CH:7]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12](=[O:17])[CH:11]=[CH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([CH:7]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12](=[O:17])[CH:11]=[CH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 7912DiisopropylamineHCID 22319851HCID 22319851, compound

Product 2

HCID 22319851HCID 22319851, compoundHCID 86592062HCID 86592062, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

0.19 g of the diastereomer (a) isolated in Example 51 was dissolved in 30 ml of dichloromethane, and to the resulting solution were added 0.20 ml of diisopropylamine and 0.70 ml of chloromethylmethylether. The resulting solution was stirred at 40° C. for one and a half hours. Adding of reagent and stirring were continued at 40° C. until TLC indicated that starting materials had been consumed. As a result, adding 0.70 ml of diisopropylethylamine and 2.4 ml of chloromethylmethylether and stirring for seven hours had been required. The reaction solution was poured into ice water and the organic phase was separated. The aqueous phase was extracted with dichloromethane. The organic phase was washed water and a saturated saline solution, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude product was purified by column chromatography on silica gel, and the eluate with ethyl acetate-hexane (1:6) was collected, to afford 0.17 g of the titled compound (a) and 10 mg of the titled compound (b) as colorless liquid.

Workup

  1. additionAdding of reagent
  2. stirringstirring
  3. customwere continued at 40° C. until TLC
  4. customhad been consumed
  5. additionAs a result, adding 0.70 ml of diisopropylethylamine and 2.4 ml of chloromethylmethylether
  6. stirringstirring for seven hours
  7. additionThe reaction solution was poured into ice water
  8. customthe organic phase was separated
  9. extractionThe aqueous phase was extracted with dichloromethane
  10. washThe organic phase was washed water
  11. dry with materiala saturated saline solution, and dried over anhydrous sodium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. customThe resulting crude product was purified by column chromatography on silica gel
  14. customthe eluate with ethyl acetate-hexane (1:6) was collected

Sources & evidence

ORD record
ord-bb27c7d68e234f7697af8690855a75a6
Source dataset
uspto-grants-2005_09
Patent number
US06949585B2

Reaction notes

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