Chloromethyl Methyl Ether → HCID 18398686, compound

HRID 1018965Notes

Reaction equation

HRID 1018965 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[CH:11]=1)[N:8]=[C:7]([CH:20]([OH:25])[CH2:21][CH:22]([CH3:24])[CH3:23])[CH:6]=[CH:5]2.[H-].[Na+].[CH3:28][O:29][CH2:30]Cl.[NH4+].[Cl-]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[CH:11]=1)[N:8]=[C:7]([CH:20]([O:25][CH2:28][O:29][CH3:30])[CH2:21][CH:22]([CH3:23])[CH3:24])[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 18398699HCID 18398699, compound

Product 1

HCID 18398686HCID 18398686, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diethyl 6-bromo-2-(1-hydroxy-3-methylbutyl)-8-quinolylphosphonate (219 mg, 0.51 mmol) (Example 19, step 3) in THF (2 mL) at 0° C. was added NaH (40 mg, 1.02 mmol, 60% in oil). To the resulting green suspension was added chloromethyl methyl ether (82 mg, 1.02 mmol). The mixture was stirred at r.t. for 1.5 h, Aqueous NH4Cl was added and the mixture was extracted with EtOAc. The organic extracts were washed with brine, dried (anhyd. MgSO4) and concentrated in vacuo. The residue was purified by chromatography on silica gel to give 170 mg (70%) of the title compound.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe organic extracts were washed with brine
  3. dry with materialdried (anhyd. MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e37b2b8ecd184b5e80ef91202c83297a
Source dataset
uspto-grants-2002_11
Patent number
US06486141B2

Reaction notes

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