Water → HCID 22260789, compound

HRID 1610061Notes

Reaction equation

HRID 1610061 reaction equation
[CH3:1][O:2][CH:3]([O:20][CH3:21])[C:4]1[CH:5]=[CH:6][C:7]([F:19])=[C:8]([CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[OH:11])[CH:9]=1.C(N(CC)CC)C.O>ClCCl.CS(C)=O>[CH3:21][O:20][CH:3]([O:2][CH3:1])[C:4]1[CH:5]=[CH:6][C:7]([F:19])=[C:8]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[O:11])[CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 22260652HCID 22260652, compound

Product 1

HCID 22260789HCID 22260789, compoundYield 77.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

In a mixture of 80 ml of dichloromethane and 80 ml of dimethylsulfoxide were dissolved 24.3 g of [5-(dimethoxymethyl)-2-fluorophenyl](3-fluorophenyl)methanol and 27.6 ml of triethylamine, and a suspension of 26.3 g of sulfur trioxide-pyridine complex in 30 ml dimethyl sulfoxide was added, followed by stirring at room temperature for 1 hour. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate for two times. The organic layer was washed with water, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:15), to give 18.7 g of the title compound as a colorless oil.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate for two times
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified
  7. customseparated by silica gel column chromatography (ethyl acetate:hexane=1:15)

Sources & evidence

ORD record
ord-4d886dc4f00c48bba05cb11c15ca5577
Source dataset
uspto-grants-2006_01
Patent number
US06982274B2

Reaction notes

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