Hydrochloric Acid → HCID 22902119, compound

HRID 1489532Notes

Reaction equation

HRID 1489532 reaction equation
C([Li])CCC.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][CH:15]=[CH:16][CH:17]=2)=[CH:9][CH:8]=1.[Cl:18][CH2:19][C:20](N(C)C)=[O:21].Cl>O1CCCC1>[F:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[O:14][C:15]([C:20](=[O:21])[CH2:19][Cl:18])=[CH:16][CH:17]=2)=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 758862-chloro-N,N-dimethylacetamideHCID 116152232-(4-Fluorophenyl)furanHCID 178418339Butyllithium

Product 1

HCID 22902119HCID 22902119, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.60 g (21.98 mmol) of n-butyllithium (2.5N in n-hexane) are added dropwise to 4.44 g (27.41 mmol) of 2-(4-fluorophenyl)furan in 40 ml of absolute tetrahydrofuran at -75° C. After stirring for 45 min, 5.21 g (42.86 mmol) of 2-chloro-N,N-dimethylacetamide in 20 ml of absolute tetrahydrofuran are added at -75° C. After 60 min, the mixture is poured into 200 ml of ice-water, neutralized at 0° C. with 2N hydrochloric acid and extracted 6× with 60 ml of ethyl acetate each time, the combined organic phases are washed 2× with 20 ml of water each time, dried over sodium sulphate and filtered, and the solvent is stripped off. The product is purified by column chromatography (280 g of silica gel 60; solvent: PE/EA 20:1), recrystallized from ethanol and digested with diisopropyl ether.

Workup

  1. waitAfter 60 min
  2. extractionextracted 6× with 60 ml of ethyl acetate each time
  3. washthe combined organic phases are washed 2× with 20 ml of water each time
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customThe product is purified by column chromatography (280 g of silica gel 60; solvent: PE/EA 20:1)
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-90035fe542704351bb684bcef6cdef32
Source dataset
uspto-grants-1997_10
Patent number
US05679678

Reaction notes

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