Trimethylsilyldiazomethane → HCID 21919163, compound

HRID 1830234Notes

Reaction equation

HRID 1830234 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:26])=[C:5]([C:17]([O:24][CH3:25])=[C:18]([O:22][CH3:23])[C:19]=1[O:20][CH3:21])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:16])=[C:11]([CH:15]=1)[C:12]([OH:14])=[O:13].[CH3:27][Si](C=[N+]=[N-])(C)C>CO.C1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]([CH3:26])=[C:5]([C:17]([O:24][CH3:25])=[C:18]([O:22][CH3:23])[C:19]=1[O:20][CH3:21])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:16])=[C:11]([CH:15]=1)[C:12]([O:14][CH3:27])=[O:13]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 22054252HCID 22054252, compound

Product 1

HCID 21919163HCID 21919163, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

5-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-hydroxybenzoic acid (0.800 g, 2.21 mmol) was dissolved in a mixed solvent of methanol (4 ml) and benzene (28 ml) and after adding thereto trimethylsilyldiazomethane (10% hexane solution) (0.303 g, 2.65 mmol), the solution was stirred at room temperature for 3 hours. The reaction solution was concentrated and the obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=3:1) to obtain the titled compound (0.800 g, 2.13 mmol, 96%).

Workup

  1. additionafter adding
  2. concentrationThe reaction solution was concentrated
  3. customthe obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-22b9faf04a964c118b61497979d8b4ee
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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