Chloromethyl Methyl Ether → HCID 66681170, compound

HRID 1817730Notes

Reaction equation

HRID 1817730 reaction equation
[F:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[C:6]([I:11])[C:3]=1[C:4]#[N:5].[H-].[Na+].[CH3:14][O:15][CH2:16]Cl>C1COCC1>[F:1][C:2]1[C:9]([O:10][CH2:14][O:15][CH3:16])=[CH:8][CH:7]=[C:6]([I:11])[C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 16125382HCID 16125382, compound

Product 1

HCID 66681170HCID 66681170, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 0° C. solution of Example 68A (250 mg, 0.95 mmol) in THF (5 mL) at room temperature was treated with NaH (25 mg, 95%, 1.05 mmol), stirred for 5 minutes, treated with chloromethyl methyl ether (0.108 mL, 1.4 mmol), stirred overnight, and partitioned between water and ethyl acetate. The organic extract was washed with brine, dried (MgSO4), filtered, and concentrated. The residue was purified by flash column chromatography on silica gel with 2% ethyl acetate/hexanes to provide 0.21 g of the desired product. Rf=0.4 (10% ethyl acetate/hexanes).

Workup

  1. stirringstirred overnight
  2. custompartitioned between water and ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography on silica gel with 2% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-d41a3d6b7664481ebe8229d5153f4039
Source dataset
uspto-grants-2009_10
Patent number
US07598283B2

Reaction notes

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