18-Crown-6 → HCID 18689507, compound

HRID 1458240Notes

Reaction equation

HRID 1458240 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([Cl:12])=[C:4]([O:13][CH2:14][C:15]#[CH:16])[N:3]=1.C1OCCOCCOCCOCCOCCOC1.[F-:35].[K+].S1(CCCC1)(=O)=O>C(OC)(C)(C)C>[Cl:12][C:5]1[C:4]([O:13][CH2:14][C:15]#[CH:16])=[N:3][C:2]([F:35])=[C:7]([C:8]([F:11])([F:10])[F:9])[CH:6]=1

Participants

6

Reactant 4

HCID 2855718-Crown-6HCID 31347SulfolaneHCID 522689Potassium FluorideHCID 18689506HCID 18689506, compound

Product 1

HCID 18689507HCID 18689507, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

47.3 g (0.175 mol) of 2,5-dichloro-6-propargyloxy-3-trifluoromethylpyridine, 0.5 g (1.89 mmol) of 18-crown-6 and 15.2 g (0.263 mol) of potassium fluoride were added to 150 ml of sulfolane and the mixture was stirred for 5 hours at 150°-155° C. After cooling, the reaction mixture was stirred with methyl tert-butyl ether and separated from the inorganic precipitate. The filtrate was extracted four times using water, dried and concentrated. The residue together with methylene chloride was filtered with suction through a silica gel frit and concentrated, giving 31.4 g (71% of theory) of the title compound of ηD24 =1.4732 (Table III, No. 3.036).

Workup

  1. temperatureAfter cooling
  2. customseparated from the inorganic precipitate
  3. extractionThe filtrate was extracted four times
  4. customdried
  5. concentrationconcentrated
  6. filtrationThe residue together with methylene chloride was filtered with suction through a silica gel frit
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-dd7eac6ecd744ecd92142ac0609c527f
Source dataset
uspto-grants-1998_12
Patent number
US05849920

Reaction notes

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