(Diethylamino)sulfur trifluoride → 2-Fluoromethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one

HRID 1900720

Reaction equation

HRID 1900720 reaction equation
O[CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3.C(N(S(F)(F)[F:24])CC)C>C(Cl)Cl>[F:24][CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 233696792-Hydroxymethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one

Product 1

HCID 233697882-Fluoromethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-oneYield 32.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

2-Hydroxymethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one (500 mg) was suspended in anhydrous methylene chloride (20 ml). To the suspension, diethylaminosulfur trifluoride (DAST) (372 mg) was added while stirring and cooling at -78° C. Subsequently, the mixture was stirred at room temperature for 30 minutes. After completion of the reaction, methylene chloride was further added thereto, and washed with aqueous sodium bicarbonate solution, and aqueous NaCl solution in this order. After drying, the solvent was distilled off to obtain 487 mg of a crude product. The crude product was purified by silica gel column chromatography (eluent=chloroform:methanol=400:1-20:1), and then by separative thin layer chromatography (developer=chloroform:methanol=10:1) to obtain a purified product, which was subjected to recrystallization using a solvent mixture of chloroform and n-hexane to obtain 163 mg of colorless needles (32%).

Workup

  1. stirringSubsequently, the mixture was stirred at room temperature for 30 minutes
  2. additionwas further added
  3. washwashed with aqueous sodium bicarbonate solution, and aqueous NaCl solution in this order
  4. customAfter drying
  5. distillationthe solvent was distilled off
  6. customto obtain 487 mg of a crude product
  7. customThe crude product was purified by silica gel column chromatography (eluent=chloroform:methanol=400:1-20:1)
  8. customby separative thin layer chromatography (developer=chloroform:methanol=10:1) to obtain a purified product, which
  9. customwas subjected to recrystallization
  10. additiona solvent mixture of chloroform and n-hexane

Sources & evidence

ORD record
ord-85f2a33677444530885fd7203c576ab0
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Linked notes

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