Methanol → Methyl 3-(4-iodophenyl)propanoate

HRID 1259140Notes

Reaction equation

HRID 1259140 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.CO.[N+](=[CH:17][Si](C)(C)C)=[N-]>C1(C)C=CC=CC=1>[I:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:17])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 2332383-(4-Iodophenyl)propanoic acid

Product 1

HCID 554150Methyl 3-(4-iodophenyl)propanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 3-(4-iodophenyl)propanoic acid (commercially available) in toluene and methanol (9:1, 0.2 M) 0° C. was added (diazomethyl)trimethylsilane (1 N solution in Et2O, 2 eq). After stirring at room temperature overnight the reaction mixture was concentrated under vacuum and the resulting crude residue was purified by chromatography (silica gel, 20-50% EtOAc in hexanes) to afford methyl 3-(4-iodophenyl)propanoate.

Workup

  1. concentrationwas concentrated under vacuum
  2. customthe resulting crude residue was purified by chromatography (silica gel, 20-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1983ae1167be43a6a304c95186d00180
Source dataset
uspto-grants-2013_06
Patent number
US08466167B2

Reaction notes

Loading…