Methoxymethyl-triphenylphosphonium chloride → HCID 67343516, compound

HRID 1669232Notes

Reaction equation

HRID 1669232 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]([F:47])([F:46])[C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[CH:42][C:41]([CH:44]=O)=[CH:40][CH:39]=2)=[CH:34][CH:33]=1.CCOC(C)=O.CCCCCC>C1COCC1>[CH3:8][O:9][CH:10]=[CH:44][C:41]1[CH:42]=[CH:43][C:38]([C:35]2[CH:36]=[CH:37][C:32]([C:31]([F:47])([F:46])[F:30])=[CH:33][CH:34]=2)=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 27827124'-(Trifluoromethyl)-4-biphenylcarbaldehydeHCID 21226206Ethyl acetate hexaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 67343516HCID 67343516, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ambient temperature suspension of potassium tert-butoxide (449 mg, 4.00 mmol) in THF (20 mL) is added (methoxymethyl)triphenylphosphonium chloride (1.37 g, 4.00 mmol) and is stirred at room temperature for 30 min. 4′-trifluoromethyl-biphenyl-4-carbaldehyde (500 mg, 2.00 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 (100 mL), dried (MgSO4), filtered, concentrated and chromatographed (40 g SiO2, 5% EtOAc/Hexanes) to yield the title compound (482 mg, 87%).

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 (100 mL)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customchromatographed (40 g SiO2, 5% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-6e82ced1bcc842f98fa3e96f92a88f3e
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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