Chloromethyl Methyl Ether → HCID 57433076, compound

HRID 546848Notes

Reaction equation

HRID 546848 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([C:9]([C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([CH3:38])[CH:32]=1)([C:12]1[CH:17]=[CH:16][C:15]([C:18]#[C:19][C:20]([OH:29])([C:25]([F:28])([F:27])[F:26])[C:21]([F:24])([F:23])[F:22])=[C:14]([CH3:30])[CH:13]=1)[CH2:10][CH3:11])[CH3:8].[CH3:39][O:40][CH2:41]Cl.[Cl-].[NH4+]>CN(C)C=O>[CH2:7]([C:9]([C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([CH3:38])[CH:32]=1)([C:12]1[CH:17]=[CH:16][C:15]([C:18]#[C:19][C:20]([O:29][CH2:39][O:40][CH3:41])([C:25]([F:26])([F:27])[F:28])[C:21]([F:24])([F:23])[F:22])=[C:14]([CH3:30])[CH:13]=1)[CH2:10][CH3:11])[CH3:8]

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 57433012HCID 57433012, compound

Product 1

HCID 57433076HCID 57433076, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (1.8 g, 13.6 mmol) was added to a solution of 4-{1-ethyl-1-[3-methyl-4-(4,4,4-trifluoro-3-hydroxy-3-trifluoromethyl-1-butynyl)-phenyl]-propyl}-2-methyl-phenol (Example 25-(1); 2.50 g, 5.45 mmol) in N,N-dimethylformamide (36 mL), and the mixture was stirred for 20 minutes. Then, methoxymethyl chloride (0.50 mL, 6.54 mmol) was added, and the mixture was stirred for one hour. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (10% ethyl acetate/hexane) to give the title compound (1.46 g, 66%).

Workup

  1. stirringthe mixture was stirred for one hour
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2c57ce98eb3a4158bb4ca98adb50a512
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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