Methoxymethyl-triphenylphosphonium chloride → 4-(2-Methoxy-1-methyl-vinyl)-3-methyl-4'-trifluoromethyl-biphenyl

HRID 1669227Notes

Reaction equation

HRID 1669227 reaction equation
CC(C)([O-])C.[K+].[Cl-].[CH3:8][O:9][CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:30][C:31]1[CH:32]=[C:33]([C:40]2[CH:45]=[CH:44][C:43]([C:46]([F:49])([F:48])[F:47])=[CH:42][CH:41]=2)[CH:34]=[CH:35][C:36]=1[C:37](=O)[CH3:38].CCOC(C)=O.CCCCCC>C1COCC1>[CH3:8][O:9][CH:10]=[C:37]([C:36]1[CH:35]=[CH:34][C:33]([C:40]2[CH:41]=[CH:42][C:43]([C:46]([F:47])([F:48])[F:49])=[CH:44][CH:45]=2)=[CH:32][C:31]=1[CH3:30])[CH3:38]

Participants

6

Reactant 4

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 21226206Ethyl acetate hexaneHCID 23665647Potassium tert-butoxideHCID 673427591-(3-Methyl-4'-trifluoromethyl-biphenyl-4-yl)-ethanone

Product 1

HCID 673421104-(2-Methoxy-1-methyl-vinyl)-3-methyl-4'-trifluoromethyl-biphenylYield 100.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a an ambient temperature suspension of potassium tert-butoxide (2.42 g, 21.56 mmol) in THF (70 mL) is added (methoxymethyl)triphenylphosphonium chloride (7.39 g, 21.56 mmol) and is stirred at room temperature for 30 min. 1-(3-methyl-4′-trifluoromethyl-biphenyl-4-yl)-ethanone (2.0 g, 7.19 mmol) is added and the reaction mixture continues to stir at room temperature. After 2 h TLC (20% EtOAc/hexane) indicates complete consumption of starting material. The reaction is quenched with saturated aqueous NH4Cl and concentrated. The residue is partitioned between EtOAc (100 mL) and water (30 mL). The aqueous layer is extracted with EtOAc (100 mL) and The combined organic layers are washed with brine, dried (MgSO4), filtered, concentrated and chromatographed (120 g SiO2, 10% EtOAc/Hexanes) to yield the title compound (2.22 g, quant.).

Workup

  1. stirringto stir at room temperature
  2. customconsumption of starting material
  3. customThe reaction is quenched with saturated aqueous NH4Cl
  4. concentrationconcentrated
  5. customThe residue is partitioned between EtOAc (100 mL) and water (30 mL)
  6. extractionThe aqueous layer is extracted with EtOAc (100 mL)
  7. washThe combined organic layers are washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customchromatographed (120 g SiO2, 10% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-77c2072cf17744559b475ccbdb1c0169
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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