Pyridine → 2-[2-(5-Fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane

HRID 2105980Notes

Reaction equation

HRID 2105980 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([C:8]([CH3:19])([CH3:18])[CH2:9][C:10]([C:14]([F:17])([F:16])[F:15])([OH:13])[CH2:11]O)[CH:7]=1.N1C=CC=CC=1.CS(Cl)(=O)=O.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.C(OCC)C.CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([C:8]([CH3:19])([CH3:18])[CH2:9][C:10]2([C:14]([F:17])([F:16])[F:15])[CH2:11][O:13]2)[CH:7]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 219489282-Hydroxy-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethyl-pentanol

Product 1

HCID 160992392-[2-(5-Fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethylpentane-1,2-diol (8.15 g) and pyridine (21.2 mL) in 50 mL of methylene chloride (CH2Cl2) at 0° C.-5° C. was added dropwise methanesulfonyl chloride (2.63 mL). The mixture was warmed to room temperature, stirred overnight and methanol (80 mL) and K2CO3 (36.2 g) were added. The mixture was stirred 4 hours, diluted with diethyl ether, washed with water, dilute HCl, and brine, and dried over magnesium sulfate. Removal of the volatiles in vacuo provided a residue that was purified by flash silica gel chromatography using 5% EtOAc in hexanes as the eluent. The product-rich fractions were collected and the volatiles removed in vacuo to provide 2-[2-(5-fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane.

Workup

  1. stirringThe mixture was stirred 4 hours
  2. washwashed with water, dilute HCl, and brine
  3. dry with materialdried over magnesium sulfate
  4. customRemoval of the volatiles in vacuo
  5. customprovided a residue that
  6. customwas purified by flash silica gel chromatography
  7. customThe product-rich fractions were collected
  8. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-0d68d9601c434532beead2c8c8c5c2e2
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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