Acetic Acid → HCID 21919196, compound

HRID 1245160Notes

Reaction equation

HRID 1245160 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:33])=[C:5]([C:24]([O:31][CH3:32])=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:11]([CH:15]=1)[C:12]([OH:14])=[O:13].[CH3:34][Si](C=[N+]=[N-])(C)C.C(O)(=O)C>CO>[CH3:1][O:2][C:3]1[C:4]([CH3:33])=[C:5]([C:24]([O:31][CH3:32])=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:11]([CH:15]=1)[C:12]([O:14][CH3:34])=[O:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 21919197HCID 21919197, compound

Product 1

HCID 21919196HCID 21919196, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-benzyloxybenzoic acid (1.22 g, 2.6548 mmol) was dissolved in methanol (100 ml), trimethylsilyl diazomethane (36.3 g, 10% solution in hexane, 31.8421 mmol) was added thereto under cooling with ice and the mixture was stirred at room temperature for 2 hours. To the reaction solution was added acetic acid (0.5 ml) and the mixture was allowed to stand at room temperature for 16 hours so as to decompose an excessive reagent. The residue obtained by concentration of the reaction solution was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give the title compound (1.18 g, 2.5321 mmol, 95%).

Workup

  1. temperatureunder cooling with ice
  2. waitto stand at room temperature for 16 hours
  3. customThe residue obtained by concentration of the reaction solution
  4. customwas purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-18ea321e6f394f53bc68df1d35c73f3a
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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