Hydrochloric Acid → HCID 16637649, compound

HRID 1489530Notes

Reaction equation

HRID 1489530 reaction equation
C([Li])CCC.[F:6][C:7]1[CH:18]=[CH:17][C:10]([O:11][C:12]2[O:13][CH:14]=[CH:15][CH:16]=2)=[CH:9][CH:8]=1.[Cl:19][CH2:20][C:21](N(C)C)=[O:22].Cl>O1CCCC1>[F:6][C:7]1[CH:18]=[CH:17][C:10]([O:11][C:12]2[O:13][C:14]([C:21](=[O:22])[CH2:20][Cl:19])=[CH:15][CH:16]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 758862-chloro-N,N-dimethylacetamideHCID 16637521HCID 16637521, compoundHCID 178418339Butyllithium

Product 1

HCID 16637649HCID 16637649, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.86 g (29.08 mmol) of n-butyllithium (2.5N in n-hexane) are added dropwise to 5.18 g (29.08 mmol) of 2-(4-fluorophenoxy)furan in 40 ml of absolute tetrahydro-furan at -75° C., and the mixture is stirred for 2.5 h. Then 6.14 g (50.51 mmol) of 2-chloro-N,N-dimethylacetamide in 30 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 5× with 40 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 (360 g of silica gel 60; solvent: toluene) and recrystallized from diisopropyl ether.

Workup

  1. waitAfter 60 min
  2. extractionextracted 5× with 40 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 (360 g of silica gel 60; solvent: toluene)
  7. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-e17a6f15f7f64466a72bb08afafa8cf8
Source dataset
uspto-grants-1997_10
Patent number
US05679678

Reaction notes

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