Potassium Iodide → HCID 22010493, compound

HRID 322996Notes

Reaction equation

HRID 322996 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:16])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:26][C:27]1[CH:31]=[CH:30][S:29][CH:28]=1>C(C(C)=O)C>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:26][C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)[CH:5]=[CH:4][C:3]=1[C:9](=[O:16])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 124874623-(Chloromethyl)thiopheneHCID 20309608HCID 20309608, compound

Product 1

HCID 22010493HCID 22010493, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A stirred solution of 4-(2,4-dihydroxyphenyl)-4-oxobutyric acid, methyl ester 6.76 g) in methyl ethyl ketone (150 mL) is treated with potassium carbonate (4.17 g), potassium iodide (5 g) tetrabutyl ammonium chloride (1 g) and 3-chloromethylthiophene (4 g), and refluxed for 24 hours. The reaction mixture is filtered, the filtrate is evaporated. The residue is dissolved in ethyl acetate, washed with water, dried, and evaporated. The residue is recrystallised from ethyl acetate/cyclohexane to give 4-(2-hydroxy-4-(thiophen-3-ylmethoxy)phenyl]-4-oxo-butyric acid, methyl ester (7.16 g), a pale cream solid, mp. 100-102° C.

Workup

  1. temperaturerefluxed for 24 hours
  2. filtrationThe reaction mixture is filtered
  3. customthe filtrate is evaporated
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washwashed with water
  6. customdried
  7. customevaporated
  8. customThe residue is recrystallised from ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-6798cf66a6de499e9c27d32e15180123
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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