Tetrahydrofuran → 5-[(4-Ethenylphenyl)oxy]-2-(trifluoromethyl)pyrimidine

HRID 474657Notes

Reaction equation

HRID 474657 reaction equation
[H-].[Na+].[F:3][C:4]([F:21])([F:20])[C:5]1[N:10]=[CH:9][C:8]([O:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=2)=[CH:7][N:6]=1.[CH2:22]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:16]([C:15]1[CH:18]=[CH:19][C:12]([O:11][C:8]2[CH:7]=[N:6][C:5]([C:4]([F:21])([F:20])[F:3])=[N:10][CH:9]=2)=[CH:13][CH:14]=1)=[CH2:22]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 866231314-{[2-(Trifluoromethyl)-5-pyrimidinyl]oxy}benzaldehyde

Product 1

HCID 677758455-[(4-Ethenylphenyl)oxy]-2-(trifluoromethyl)pyrimidineYield 60.4%

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Conditions

Temperature
0 °C

Procedure

To a suspension of NaH (373 mg, 9.32 mmol) and methyltriphenylphosphonium bromide (799 mg, 2.237 mmol) in THF (5 mL), which was stirred at 0° C. for 1 h was added 4-{[2-(trifluoromethyl)-5-pyrimidinyl]oxy}benzaldehyde (500 mg, 1.864 mmol). The mixture was stirred at room temperature for 2 h, and then quenched with NH4Cl sat. solution. The organic layer was separated and the aqueous phase was extracted with DCM. The organic phase was dried over sodium sulfate, filtered, and concentrated. Purification via flash chromatography then afforded the title compound (300 mg, 1.127 mmol, 60.4% yield).

Workup

  1. stirringThe mixture was stirred at room temperature for 2 h
  2. customquenched with NH4Cl sat. solution
  3. customThe organic layer was separated
  4. extractionthe aqueous phase was extracted with DCM
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification via flash chromatography

Sources & evidence

ORD record
ord-d21254a84f1a47ddb7ab5bfff55aa760
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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