(Diethylamino)sulfur trifluoride → 2,5-Di(4-pyridyl)-3-fluoromethyl-4-methylthiophene

HRID 2121729Notes

Reaction equation

HRID 2121729 reaction equation
O[CH2:2][C:3]1[C:7]([CH3:8])=[C:6]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[S:5][C:4]=1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.CCN(S(F)(F)[F:27])CC>C(Cl)Cl>[N:18]1[CH:19]=[CH:20][C:15]([C:4]2[S:5][C:6]([C:9]3[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=3)=[C:7]([CH3:8])[C:3]=2[CH2:2][F:27])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 23434113HCID 23434113, compound

Product 1

HCID 234340962,5-Di(4-pyridyl)-3-fluoromethyl-4-methylthiophene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of diethylaminosuifer trifluoride (DAST, 0.06 mL) in CH2Cl2 (5 mL) was added 3-hydroxymethyl-2,5-di(4-pyridyl)-4-methylthiophene (0.144 g) at 0° C. under nitrogen. The resulting mixture was stirred at room temperature for 1 hour. DAST (0.06 mL) was additionally added to the reaction mixture, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into ice-water and the whole was extracted with CH2Cl2 (50 mL). The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatographyeiuting with ethyl acetate-CH2Cl2 (1:1). The resulting solid was recrystallized from diisoplopanol-diisopropyl ether to give the title compound (0.056 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. extractionthe whole was extracted with CH2Cl2 (50 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatographyeiuting with ethyl acetate-CH2Cl2 (1:1)
  7. customThe resulting solid was recrystallized from diisoplopanol-diisopropyl ether

Sources & evidence

ORD record
ord-e0497eeb27984e25b0dc857dfc5df62a
Source dataset
uspto-grants-2004_02
Patent number
US06696470B2

Reaction notes

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