Potassium Carbonate → HCID 23335152, compound

HRID 903803Notes

Reaction equation

HRID 903803 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH:7]2[CH:9]([C:10]([OH:12])=[O:11])[C:8]2([CH3:14])[CH3:13])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)P(=O)(N(C)C)N(C)C.[CH3:34][C:35]1[CH:36]=[C:37]([CH:46]=[CH:47][CH:48]=1)[CH2:38][C:39]1[CH:43]=[CH:42][NH:41][C:40]=1[CH2:44]Br>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]2[CH:9]([C:10]([O:12][CH2:44][C:40]3[NH:41][CH:42]=[CH:43][C:39]=3[CH2:38][C:37]3[CH:46]=[CH:47][CH:48]=[C:35]([CH3:34])[CH:36]=3)=[O:11])[C:8]2([CH3:13])[CH3:14])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 12679HexamethylphosphoramideHCID 203049613-(4-Chlorophenoxy)-2,2-dimethylcyclopropanecarboxylic acidHCID 23335163HCID 23335163, compound

Product 1

HCID 23335152HCID 23335152, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylic acid (2.77 mmol), potassium carbonate (3.25 mmol) and hexamethylphosphoric triamide (HMPT) (3 ml), with stirring and under nitrogen, at RT, is added 3-(3-methylbenzyl)-pyrrolylmethyl bromide (2.77 mmol) in THF. The reaction is stirred at RT for about 48 hours and then worked up by partition between water/ether. The organic phase is washed with water and brine, dried over potassium carbonate, filtered and the solvent is removed from the filtrate. The residue is plated on preparatory TLC plates developing with 10% ether/hexane to yield 3-(3-methylbenzyl)-pyrrolylmethyl 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylate.

Workup

  1. stirringThe reaction is stirred at RT for about 48 hours
  2. customby partition between water/ether
  3. washThe organic phase is washed with water and brine
  4. dry with materialdried over potassium carbonate
  5. filtrationfiltered
  6. customthe solvent is removed from the filtrate

Sources & evidence

ORD record
ord-7796e215005a42ca8739a7e7e6b8e597
Source dataset
uspto-grants-1980_10
Patent number
US04229352

Reaction notes

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