Methoxymethyl-triphenylphosphonium chloride → HCID 69615387, compound

HRID 495526Notes

Reaction equation

HRID 495526 reaction equation
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[K+].[Cl-].[CH3:12][O:13][CH2:14][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[F:34][C:35]1[CH:53]=[CH:52][CH:51]=[C:50]([F:54])[C:36]=1[CH2:37][N:38]1[C:43]([CH3:44])=[C:42](C=O)[C:41](=[O:47])[C:40]([Br:48])=[C:39]1[CH3:49]>C1(C)C=CC=CC=1.C1COCC1>[F:54][C:50]1[CH:51]=[CH:52][CH:53]=[C:35]([F:34])[C:36]=1[CH2:37][N:38]1[C:43]([CH3:44])=[C:42]([CH:1]=[CH:14][O:13][CH3:12])[C:41](=[O:47])[C:40]([Br:48])=[C:39]1[CH3:49]

Participants

6

Reactant 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 223272251-(2,6-Difluorobenzyl)-2,6-dimethyl-3-bromo-5-formyl-4-pyridone

Product 1

HCID 69615387HCID 69615387, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

KHMDS (2.4 mmol, 4.8 mL of a 0.5 M solution in toluene) was added dropwise to a vigorously stirred suspension of (methoxymethyl)triphenylphosphonium chloride (771 mg, 2.25 mmol) in anhydrous THF (8 mL), at −78° C. under N2. The resulting orange suspension was stirred at −78° C. for 45 min. Then, a solution of 1-(2,6-difluorobenzyl)-2,6-dimethyl-3-bromo-5-formyl-4-pyridone (534 mg, 1.50 mmol) in THF (8 mL) was added dropwise and the reaction was allowed to warm slowly to room temperature. After 1 h at room temperature, the reaction was quenched with an aqueous saturated solution of NaHCO3. The organics were extracted with EtOAc (50 mL), the organic layer was separated, washed with H2O and brine, dried over MgSO4, filtered and evaporated under vacuum. The crude residue was utilized in the next step. LRMS m/z 384.0 (M+−1), 386.0 (M++1).

Workup

  1. temperatureto warm slowly to room temperature
  2. waitAfter 1 h at room temperature
  3. customthe reaction was quenched with an aqueous saturated solution of NaHCO3
  4. extractionThe organics were extracted with EtOAc (50 mL)
  5. customthe organic layer was separated
  6. washwashed with H2O and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-900fce02e0ea45feb6eca1a3c19477d6
Source dataset
uspto-grants-2005_09
Patent number
US06939883B2

Reaction notes

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