Ethanol → 3-Ethyl-4,6-dihydroxy-2-(methoxycarbonylmethyl)benzoic acid methyl ester

HRID 505667Notes

Reaction equation

HRID 505667 reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH:4]=[C:5]=[CH:6][C:7]([O:9][CH3:10])=[O:8].C([O:14][C:15](O[Si](C)(C)C)=[CH:16][C:17]([O:21][Si](C)(C)C)=[CH:18][CH2:19][CH3:20])C.C(O)C.[F-].[NH4+]>O>[CH3:10][O:9][C:7](=[O:8])[C:6]1[C:15]([OH:14])=[CH:16][C:17]([OH:21])=[C:18]([CH2:19][CH3:20])[C:5]=1[CH2:4][C:3]([O:2][CH3:1])=[O:11]

Participants

6

Reactant 4

HCID 702EthanolHCID 25516Ammonium fluorideHCID 637810Dimethyl penta-2,3-dienedioateHCID 729526991-Ethoxy-1,3-bis(trimethylsiloxy)hexa-1,3-diene

Product 1

HCID 115363173-Ethyl-4,6-dihydroxy-2-(methoxycarbonylmethyl)benzoic acid methyl esterYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The above-obtained penta-2,3-dienedioic acid dimethyl ester (4.6 g, 30 mmol) and 1-ethoxy-1,3-bis(trimethylsiloxy)hexa-1,3-diene (13 g, 41 mmol) were mixed and stirred at a room temperature for 1.5 hours. The reaction mixture was added with ethanol (100 mL) and ammonium fluoride (5.4 g) and stirred at a room temperature for 2 hours. The reaction mixture was further added with water and extracted with ethyl acetate 3 times. The organic layers were combined, sequentially washed with water and saturated brine, dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure. The residue was triturated with hexane (50 mL) to obtain Compound 23 (3.2 g, 40%).

Workup

  1. stirringstirred at a room temperature for 2 hours
  2. extractionextracted with ethyl acetate 3 times
  3. washsequentially washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was triturated with hexane (50 mL)

Sources & evidence

ORD record
ord-8da847751b78430b91614233e4d53ef2
Source dataset
uspto-grants-2010_08
Patent number
US07781485B2

Reaction notes

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