Potassium Bicarbonate → HCID 23335159, compound

HRID 903800Notes

Reaction equation

HRID 903800 reaction equation
[F: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+].CS(O[CH2:27][C:28]1[NH:29][CH:30]=[CH:31][C:32]=1[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=O)=O>C1COCC1.CN(C=O)C.CCOCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]2[CH:9]([C:10]([O:12][CH2:27][C:28]3[NH:29][CH:30]=[CH:31][C:32]=3[CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:11])[C:8]2([CH3:13])[CH3:14])=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 516893Potassium BicarbonateHCID 20304939HCID 20304939, compoundHCID 23335145HCID 23335145, compound

Product 1

HCID 23335159HCID 23335159, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent2×

Procedure

3-(4-Fluorophenoxy)-2,2-dimethylcyclopropanecarboxylic acid (3.40 mmol) is stirred together with 0.34 g (3.40 mmol) potassium bicarbonate in 10 ml THF/DMF (1:1) for 15 minutes. Then 3.40 mmol of 3-benzylpyrrolylmethyl methanesulfonate in 5 ml THF/DMF (1:1) is added and the mixture stirred for approximately 48 hours. The reaction is diluted with ether, washed with water (3X) and sat. NaCl, dried and solvent is removed. The crude product is purified by preparative TLC developing with 10% ethyl acetate/hexane to yield 3-benzylpyrrolylmethyl 3-(4-fluorophenoxy)-2,2-dimethylcyclopropanecarboxylate.

Workup

  1. washwashed with water (3X) and sat. NaCl
  2. customdried
  3. customsolvent is removed
  4. customThe crude product is purified by preparative TLC

Sources & evidence

ORD record
ord-0def8203dc604d0484b9fa0ca8a228b8
Source dataset
uspto-grants-1980_10
Patent number
US04229352

Reaction notes

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