Triethylsilane → 3-[4-(2,3,4,5-tetramethoxy-6-methylbenzyl)phenyl]acrylic Acid Ethylester

HRID 496328Notes

Reaction equation

HRID 496328 reaction equation
C([SiH](CC)CC)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[CH2:20]([O:22][C:23](=[O:52])[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32](OC(=O)C)[C:33]2[C:38]([CH3:39])=[C:37]([O:40][CH3:41])[C:36]([O:42][CH3:43])=[C:35]([O:44][CH3:45])[C:34]=2[O:46][CH3:47])=[CH:28][CH:27]=1)[CH3:21]>C(Cl)Cl>[CH2:20]([O:22][C:23](=[O:52])[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C:33]2[C:38]([CH3:39])=[C:37]([O:40][CH3:41])[C:36]([O:42][CH3:43])=[C:35]([O:44][CH3:45])[C:34]=2[O:46][CH3:47])=[CH:28][CH:27]=1)[CH3:21]

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 65367Trimethylsilyl triflateHCID 86759842HCID 86759842, compound

Product 1

HCID 867598433-[4-(2,3,4,5-tetramethoxy-6-methylbenzyl)phenyl]acrylic Acid EthylesterYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of triethylsilane (720 mg, 6.21 mmol) and trimethylsilyl trifluoromethanesulfonate (TMSOTf) in methylene chloride (250 ml) was added dropwise a solution of the compound (2.37 g, 5.17 mmol) obtained in Step 3 in methylene chloride (50 ml) and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with water, dried, and then the solvent was distilled off. The residue was purified by a silica gel column chromatography (hexane:ethyl acetate=4:1) to yield the title compound (1.90 g, 4.74 mmol, yield 92%).

Workup

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

Sources & evidence

ORD record
ord-2f573344a9524ffabf36dd055e848738
Source dataset
uspto-grants-2005_09
Patent number
US06943196B1

Reaction notes

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