Potassium Iodide → 4-(3-tert-Butoxycarbonyl-propoxy)-3-methyl-benzoic Acid Methyl Ester

HRID 220856

Reaction equation

HRID 220856 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH3:9][O:10][C:11](=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH3:19])[CH:13]=1.[C:21]([O:25][C:26](=[O:31])[CH2:27][CH2:28][CH2:29]Br)([CH3:24])([CH3:23])[CH3:22]>CC(C)=O>[CH3:9][O:10][C:11](=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:29][CH2:28][CH2:27][C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:31])=[C:14]([CH3:19])[CH:13]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 2757253tert-Butyl 4-bromobutanoateHCID 11240684Methyl 4-hydroxy-3-methylbenzoate

Product 1

HCID 575554224-(3-tert-Butoxycarbonyl-propoxy)-3-methyl-benzoic Acid Methyl EsterYield 76%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (580 mg, 4.20 mmol) and potassium iodide (72 mg, 0.43 mmol) were added to a solution of 4-hydroxy-3-methyl-benzoic acid methyl ester from Example E29 (293 mg, 1.76 mmol) and 4-bromo-butyric acid tert-butyl ester from Example E42.1 (397 mg, 1.78 mmol) in acetone (50 ml). The mixture was heated at reflux for 18 h then the solid was filtered off and the filtrate concentrated in vacuo. The residue was dissolved in EtOAc, washed with water then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 20% EtOAc:80% pet. ether) to yield the title compound (414 mg, 76%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 h
  3. filtrationthe solid was filtered off
  4. concentrationthe filtrate concentrated in vacuo
  5. dissolutionThe residue was dissolved in EtOAc
  6. washwashed with water
  7. dry with materialbrine, dried
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography on silica gel (eluant; 20% EtOAc:80% pet. ether)

Sources & evidence

ORD record
ord-287836c0791d43c3aa7010c816677da8
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Linked notes

Loading…