Methoxymethyl-triphenylphosphonium chloride → HCID 67342613, compound

HRID 1669229Notes

Reaction equation

HRID 1669229 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.[F:30][C:31]1[CH:32]=[C:33]([C:39]2[CH:44]=[CH:43][C:42]([C:45]([F:48])([F:47])[F:46])=[CH:41][CH:40]=2)[CH:34]=[CH:35][C:36]=1[CH:37]=O.CCOC(C)=O.CCCCCC>C1COCC1>[F:30][C:31]1[CH:32]=[C:33]([C:39]2[CH:44]=[CH:43][C:42]([C:45]([F:48])([F:47])[F:46])=[CH:41][CH:40]=2)[CH:34]=[CH:35][C:36]=1[CH:37]=[CH:8][O:9][CH3:10]

Participants

6

Reactant 4

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 21226206Ethyl acetate hexaneHCID 21936374HCID 21936374, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 67342613HCID 67342613, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a an ambient temperature suspension of potassium tert-butoxide (419 mg, 3.73 mmol) in THF (20 mL) is added (methoxymethyl)triphenylphosphonium chloride (1.28 g, 3.73 mmol) and is stirred at room temperature for 30 min. 3-Fluoro-4′-trifluoromethyl-biphenyl-4-carbaldehyde (500 mg, 1.87 mmol) is added and the reaction mixture continues to stir at room temperature. After 2 h TLC (30% EtOAc/hexane) indicates complete consumption of starting material. The reaction is quenched with saturated aqueous NH4Cl and concentrated. The residue is partitioned between EtOAc (50 mL) and water (20 mL). The aqueous layer is extracted with EtOAc (50 mL) and the combined organic layers are washed with brine, dried (MgSO4), filtered, concentrated and chromatographed (120 g SiO2, 5% EtOAc/Hexanes) to yield the title compound (474 mg, 85%).

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 (50 mL) and water (20 mL)
  6. extractionThe aqueous layer is extracted with EtOAc (50 mL)
  7. washthe combined organic layers are washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customchromatographed (120 g SiO2, 5% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-33bea200aecd46f99a7009a1af9ef91d
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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