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

HRID 705896Notes

Reaction equation

HRID 705896 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-b631c9e093a147968e6e73c0f69ea87e
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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