Trimethylsilyldiazomethane → Methyl 3-(3-hydroxypropyl)-4,5-dimethoxybenzoate

HRID 638917Notes

Reaction equation

HRID 638917 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([O:16][CH3:17])[C:13]=1[O:14][CH3:15])[C:8]([OH:10])=[O:9].[CH3:18][Si](C=[N+]=[N-])(C)C>CO>[CH3:18][O:9][C:8](=[O:10])[C:7]1[CH:11]=[C:12]([O:16][CH3:17])[C:13]([O:14][CH3:15])=[C:5]([CH2:4][CH2:3][CH2:2][OH:1])[CH:6]=1

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 686851493-(3-Hydroxypropyl)-4,5-dimethoxybenzoic acid

Product 1

HCID 68686246Methyl 3-(3-hydroxypropyl)-4,5-dimethoxybenzoateYield 73.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 3-(3-hydroxypropyl)-4,5-dimethoxybenzoic acid (Example 10, Step 1, 3.53 g, 14.7 mmol) in MeOH (37 mL) at 0° C. was slowly added trimethylsilyldiazomethane (TMSCHN2) (2.0 M, 37 mL, 73.5 mmol) over the course of 5 min. After stirring for 10 min the reaction mixture was concentrated. The crude product was purified by flash column chromatography on silica gel using 67% EtOAc in hexanes as an eluent to furnish 3-(3-hydroxypropyl)-4,5-dimethoxybenzoic acid methyl ester (2.76 g).

Workup

  1. customat 0° C.
  2. customover the course of 5 min
  3. concentrationwas concentrated
  4. customThe crude product was purified by flash column chromatography on silica gel using 67% EtOAc in hexanes as an eluent

Sources & evidence

ORD record
ord-804ba8a37a84493f848fc20e1379a0af
Source dataset
uspto-grants-2010_04
Patent number
US07691843B2

Reaction notes

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