Tetrahydrofuran → HCID 70148215, compound

HRID 2302139Notes

Reaction equation

HRID 2302139 reaction equation
[CH3:1][N:2]1[C:6]([OH:7])=[CH:5][CH:4]=[N:3]1.C(=O)([O-])[O-].[K+].[K+].O1CCCC1.[Cl:19][C:20]1[C:29]([CH2:30]Br)=[C:28]([S:32]([CH3:35])(=[O:34])=[O:33])[CH:27]=[CH:26][C:21]=1[C:22]([O:24][CH3:25])=[O:23]>C(OCC)(=O)C>[Cl:19][C:20]1[C:29]([CH2:30][O:7][C:6]2[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=2)=[C:28]([S:32]([CH3:35])(=[O:34])=[O:33])[CH:27]=[CH:26][C:21]=1[C:22]([O:24][CH3:25])=[O:23]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 11430Potassium CarbonateHCID 10969914Methyl 3-bromomethyl-2-chloro-4-methylsulfonylbenzoateHCID 178481816HCID 178481816, compound

Product 1

HCID 70148215HCID 70148215, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

4.3 g (44 mmol) of 1-methyl-5-hydroxypyrazol, 9.1 g of potassium carbonate and 100 ml of tetrahydrofurane are heated at 65° C. for 1 h. 15 g (44 mmol) of methyl 2-chloro-3-bromomethyl-4-methylsulfonylbenzoate and 150 ml of tetrahydrofurane are added to this mixture and heated at 40° C. for 4 h. This mixture is stirred for 12 h, freed from the solvent under reduced pressure, taken up in ethyl acetate, washed with sodium bicarbonate solution and water, dried and freed form the solvent. The crude product is purified over silica gel (eluent: cyclohexane/ethyl acetate=1/1). Yield: 7.6 g; m.p. 70° C.

Workup

  1. washwashed with sodium bicarbonate solution and water
  2. customdried
  3. customThe crude product is purified over silica gel (eluent: cyclohexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-49c2f9efb2e748b69c606b895398e003
Source dataset
uspto-grants-2002_08
Patent number
US06432881B1

Reaction notes

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