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

HRID 430465Notes

Reaction equation

HRID 430465 reaction equation
O[C:2]([C:18]([F:21])([F:20])[F:19])([CH2:5][C:6]([C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[O:16][CH3:17])([CH3:8])[CH3:7])[CH2:3][OH:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C>O1CCCC1>[F:15][C:13]1[CH:12]=[CH:11][C:10]([O:16][CH3:17])=[C:9]([C:6]([CH3:8])([CH3:7])[CH2:5][C:2]2([C:18]([F:21])([F:20])[F:19])[CH2:3][O:4]2)[CH:14]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 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 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.5 g of 2-hydroxy-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-trifluoromethyl-pentanol and 3.45 g of triphenylphosphine are dissolved in 50 ml of tetrahydrofuran and mixed in 3 portions at 0° C. with 2.5 ml of azodicarboxylic acid-diethyl ester. After one hour at 0° C., it is stirred for 16 more hours at room temperature, then refluxed for 7 hours and again stirred for 48 hours at room temperature. After concentration by evaporation, a hexane-isopropylether mixture is added, filtered, and the filtrate is chromatographed on silica gel. The product that is eluted with hexane/ethyl acetate is distilled on a bulb tube, boiling point 100° C./0.5 mbar.

Workup

  1. temperaturerefluxed for 7 hours
  2. stirringagain stirred for 48 hours at room temperature
  3. concentrationAfter concentration
  4. customby evaporation
  5. additiona hexane-isopropylether mixture is added
  6. filtrationfiltered
  7. customthe filtrate is chromatographed on silica gel
  8. washThe product that is eluted with hexane/ethyl acetate
  9. distillationis distilled on a bulb tube

Sources & evidence

ORD record
ord-5b5d00e4d1e94e00b2e5f38aa16499ac
Source dataset
uspto-grants-2001_11
Patent number
US06323199B1

Reaction notes

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