HCID 68379485, compound → HCID 68379228, compound

HRID 1410062Notes

Reaction equation

HRID 1410062 reaction equation
[CH3:1][C:2]1([CH3:27])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:10]=[C:11]([CH:24]=[CH:25][CH:26]=2)/[CH:12]=[CH:13]/[C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=2)[O:3]1>CO.O=[Pt]=O>[CH3:7][C:6]1([CH3:8])[C:2]([CH3:1])([CH3:27])[O:3][B:4]([C:9]2[CH:10]=[C:11]([CH:24]=[CH:25][CH:26]=2)[CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:22][CH:23]=2)[O:5]1

Participants

4

Reactant 1

HCID 68379485HCID 68379485, compound

Product 1

HCID 68379228HCID 68379228, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture of (E)-methyl 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)styryl)benzoate (200 mg, 0.55 mmol) and PtO2 (50 mg, 0.22 mmol) in 30 mL of MeOH was stirred at room temperature for 18 hours under H2 atmosphere. The solvent was evaporated and the residue was purified by silica gel chromatography (200-300 mesh, eluting with a mixture of petroleum ether and ethyl acetate=50:1) to give methyl 4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenethyl)benzoate (90 mg, 50%) as a colorless oil

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by silica gel chromatography (200-300 mesh
  3. washeluting with a mixture of petroleum ether and ethyl acetate=50:1)

Sources & evidence

ORD record
ord-c1de6794473a4289b4f6524b40cf94a3
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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