Water → HCID 88065593, compound

HRID 1936544Notes

Reaction equation

HRID 1936544 reaction equation
CS(O[CH2:6][C:7]#[CH:8])(=O)=O.[Cl:9][C:10]1[C:15]([OH:16])=[CH:14][C:13]([C:17]2[C:21]([Cl:22])=[C:20]([C:23]([F:26])([F:25])[F:24])[N:19]([CH3:27])[C:18]=2[Cl:28])=[C:12]([F:29])[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].O>CC(CC(C)C)=O>[Cl:9][C:10]1[C:15]([O:16][CH2:8][C:7]#[CH:6])=[CH:14][C:13]([C:17]2[C:21]([Cl:22])=[C:20]([C:23]([F:26])([F:25])[F:24])[N:19]([CH3:27])[C:18]=2[Cl:28])=[C:12]([F:29])[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 305925propargyl mesylateHCID 11233803HCID 11233803, compound

Product 1

HCID 88065593HCID 88065593, compoundYield 39.9%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

2-propinyl methanesulfonate (0.35 g; 2.6 mmoles) is added to a mixture of 3-(4-chloro-2-fluoro-5-hydroxyphenyl) -2,4-dichloro-1-methyl-5-trifluoromethyl pyrrole (0.9 g; 2.5 mmoles) and potassium carbonate (0.33 g; 2.39 mmoles) in methylisobutylketone (10 ml). The mixture is heated to 80° C. for 3 hours. The reaction mixture is poured into water (10 ml), extracted with ethyl ether (3×20 ml), the ether phase is washed with a saturated solution of sodium chloride, anhydrified with sodium sulfate and concentrated in a rotavapor. The raw product obtained (1.0 g) is chromatographed on silica gel, eluating with n-hexane/ethyl acetate 90:10. 0.40 g of solid white product are obtained.

Workup

  1. extractionextracted with ethyl ether (3×20 ml)
  2. washthe ether phase is washed with a saturated solution of sodium chloride
  3. concentrationconcentrated in a rotavapor
  4. customThe raw product obtained (1.0 g)
  5. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-080038f8ca8e4b169d46cabc089265f4
Source dataset
uspto-grants-2002_05
Patent number
US06391827B1

Reaction notes

Loading…