Triethylsilane → 4-(2,3,4,5-tetramethoxy-6-methylbenzyl)benzoic Acid Methylester

HRID 496352Notes

Reaction equation

HRID 496352 reaction equation
[CH2:1]([SiH](CC)CC)C.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.[CH3:20][O:21][C:22]1[C:37]([O:38][CH3:39])=[C:36]([O:40][CH3:41])[C:35]([O:42][CH3:43])=[C:34]([CH3:44])[C:23]=1[CH2:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=1>C(Cl)Cl>[CH3:1][O:30][C:29](=[O:31])[C:28]1[CH:27]=[CH:26][C:25]([CH2:24][C:23]2[C:34]([CH3:44])=[C:35]([O:42][CH3:43])[C:36]([O:40][CH3:41])=[C:37]([O:38][CH3:39])[C:22]=2[O:21][CH3:20])=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 65367Trimethylsilyl triflateHCID 223252774-(2,3,4,5-tetramethoxy-6-methylbenzyl)benzoic Acid

Product 1

HCID 537286504-(2,3,4,5-tetramethoxy-6-methylbenzyl)benzoic Acid MethylesterYield 71.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of triethylsilane (88 mg, 0.76 mmol) and TMSOTf (0.004 ml) in methylene chloride (2 ml) was added dropwise a solution of the compound (237 mg, 0.63 mmol) obtained in Step 2 in methylene chloride (2 ml) and the mixture was stirred at room temperature for 4 hours. The reaction mixture was washed with saturated saline, dried, and then the solvent was distilled off. The residue was purified by a silica gel column chromatography (ethyl acetate:hexane=1:6) to yield the title compound (160 mg, 0.45 mmol, yield 71%).

Workup

  1. washThe reaction mixture was washed with saturated saline
  2. customdried
  3. distillationthe solvent was distilled off
  4. customThe residue was purified by a silica gel column chromatography (ethyl acetate:hexane=1:6)

Sources & evidence

ORD record
ord-1f35c6498e2546d1a62c6773bbcd741d
Source dataset
uspto-grants-2005_09
Patent number
US06943196B1

Reaction notes

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