Chloromethyl Methyl Ether → HCID 59134395, compound

HRID 2425359Notes

Reaction equation

HRID 2425359 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:5]=1[OH:11])([O-:3])=[O:2].[CH3:12][O:13][CH2:14]Cl.[CH:16](N(C(C)C)CC)(C)C.[Cl-].[NH4+].[H-].[Na+].[CH3:29][CH:30]([OH:34])[C:31]#[C:32]C>O1CCCC1.CC(N(C)C)=O>[CH3:12][O:13][CH2:14][O:11][C:5]1[CH:6]=[C:7]([O:34][C:30]([CH3:16])([CH3:29])[C:31]#[CH:32])[CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

9

Reactant 6

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 25517Ammonium Chloride2×HCID 81531DiisopropylethylamineHCID 1362364-Fluoro-2-nitrophenolHCID 1413443-Pentyn-2-ol

Product 1

HCID 59134395HCID 59134395, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 2-nitro-4-fluorophenol (1.6 g, 10.2 mmol) in tetrahydrofuran (32 mL), chloromethyl methyl ether (1.23 g, 15.3 mmol) and di-isopropyl ethyl amine (2.66 mL, 15.3 mmol) were added at room temperature, and the resulting mixture was stirred at room temperature for 1 hour. Upon the completion of the reaction, saturated ammonium chloride aqueous solution was added thereto, the resulting solution was extracted with ethyl acetate, washed with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. Sodium hydride (553 mg, 12.3 mmol) and 1-methyl-2-butyn-1-ol (1.23 mL, 12.7 mmol) were added to the solution of the resulting mixture in dimethylacetamide (17 mL) at 0° C., and the resulting mixture was stirred for 7 hours. Upon the completion of the reaction, saturated ammonium chloride aqueous solution was added thereto, the resulting solution was extracted with ethyl acetate, washed with saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. The resulting mixture was purified by silica gel column (hexane/ethyl acetate=5/1) and the aimed product was obtained (yield: 94%).

Workup

  1. additionwas added
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. stirringthe resulting mixture was stirred for 7 hours
  7. additionwas added
  8. extractionthe resulting solution was extracted with ethyl acetate
  9. washwashed with saturated sodium chloride solution
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated
  12. customThe resulting mixture was purified by silica gel column (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-ef5720affe314aad85b9a4f4940e2311
Source dataset
uspto-grants-2011_06
Patent number
US07964623B2

Reaction notes

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