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

HRID 1004179Notes

Reaction equation

HRID 1004179 reaction equation
C(N(S(F)(F)[F:7])CC)C.O[CH2:11][C:12]1[C:16]([CH3:17])=[C:15]([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[S:14][C:13]=1[C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1>C(Cl)Cl>[N:27]1[CH:28]=[CH:29][C:24]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[C:16]([CH3:17])[C:12]=2[CH2:11][F:7])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluoride2×HCID 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 diethylaminosulfer 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 chromatography eluting 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 chromatography
  7. washeluting with ethyl acetate-CH2Cl2 (1:1)
  8. customThe resulting solid was recrystallized from diisoplopanol-diisopropyl ether

Sources & evidence

ORD record
ord-8ac965bcbca94020904d2e9c530a44a4
Source dataset
uspto-grants-2000_04
Patent number
US06048880

Reaction notes

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