Triethylamine → 2-(Dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)benzyl methanesulfonate

HRID 2076631Notes

Reaction equation

HRID 2076631 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][CH:10]([O:27][CH3:28])[C:11]1[C:16]([O:17][CH2:18][O:19][CH3:20])=[C:15]([C:21]([F:24])([F:23])[F:22])[CH:14]=[CH:13][C:12]=1[CH2:25][OH:26].[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C(OCC)(=O)C>[CH3:29][S:30]([O:26][CH2:25][C:12]1[CH:13]=[CH:14][C:15]([C:21]([F:22])([F:23])[F:24])=[C:16]([O:17][CH2:18][O:19][CH3:20])[C:11]=1[CH:10]([O:9][CH3:8])[O:27][CH3:28])(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67119352[2-(Dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)phenyl]methanol

Product 1

HCID 866174072-(Dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)benzyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (2.74 ml, 19.7 mmol) was added to a solution of [2-(dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)phenyl]methanol (5.09 g, 16.4 mmol) obtained in Example (6-6) in ethyl acetate (50 ml). After methanesulfonyl chloride (1.33 ml, 17.2 mmol) was added dropwise to the mixture under ice-cooling, the reaction mixture was stirred at the same temperature for 30 minutes. The reaction mixture was filtered through Celite. The filtrate was successively washed with a saturated aqueous sodium hydrogencarbonate solution, water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. n-Hexane was added to the residue obtained by removing the solvent under reduced pressure. The precipitated crystals were filtered to give 2-(dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)benzyl methanesulfonate as a pale yellow compound (5.37 g, yield: 84%).

Workup

  1. temperaturecooling
  2. filtrationThe reaction mixture was filtered through Celite
  3. washThe filtrate was successively washed with a saturated aqueous sodium hydrogencarbonate solution, water
  4. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  5. additionn-Hexane was added to the residue
  6. customobtained
  7. customby removing the solvent under reduced pressure
  8. filtrationThe precipitated crystals were filtered

Sources & evidence

ORD record
ord-68e2d28eaa1740aeac428db8951a1641
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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