Potassium Carbonate → HCID 20344555, compound

HRID 2049829Notes

Reaction equation

HRID 2049829 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.[CH2:34]([C:41]1[O:45][CH:44]=[C:43]([CH2:46]Br)[CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]2[CH:9]([C:10]([O:12][CH2:46][C:43]3[CH:42]=[C:41]([CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[O:45][CH:44]=3)=[O:11])[C:8]2([CH3:13])[CH3:14])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 12679HexamethylphosphoramideHCID 14346725HCID 14346725, compoundHCID 203049613-(4-Chlorophenoxy)-2,2-dimethylcyclopropanecarboxylic acid

Product 1

HCID 20344555HCID 20344555, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylic acid (2.77 mmol) (as prepared in, for example, Example 1 or 2), potassium carbonate (3.25 mmol) and hexamethylphosphoric triamide (HMPT) (3 ml), with stirring and under nitrogen, at RT, is added 5-benzyl-3-furylmethyl bromide (2.77 mmol) in THF. The reaction is stirred at RT for about 48 hr 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 prep. TLC plates developing with 10% ether/hexane to yield 5-benzyl-3-furylmethyl 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylate.

Workup

  1. stirringThe reaction is stirred at RT for about 48 hr
  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-c0ff35bb19204896bdbfd7f2007c6afa
Source dataset
uspto-grants-1980_04
Patent number
US04198527

Reaction notes

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