Tributylstannane → (E)-2-(tributylstannyl)-3-(3,4-dimethoxyphenyl)acrylamide

HRID 736865Notes

Reaction equation

HRID 736865 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]([NH2:15])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH2:16]([SnH:20]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19]>O1CCCC1>[CH2:25]([Sn:20]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:21][CH2:22][CH2:23][CH3:24])/[C:12](=[CH:11]/[C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)/[C:13]([NH2:15])=[O:14])[CH2:26][CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 5948TributylstannaneHCID 8833563-(3,4-Dimethoxyphenyl)propanamide

Product 1

HCID 11965057(E)-2-(tributylstannyl)-3-(3,4-dimethoxyphenyl)acrylamideYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-(3,4-dimethoxyphenyl)propionic acid amide (20.5 mg, 0.1 mmol) prepared in the same manner as in Reference Synthetic Example 8 was dissolved in tetrahydrofuran (2 ml) in nitrogen atmosphere, and under cooling with ice, tetrakistriphenylphosphine palladium(0) (5 mg, 0.004 mmol) was added, and then a tetrahydrofuran solution (0.5 ml) of tri-n-butyltin hydride (35 μl, 0.13 mmol) was dropwise added. After stirring for 30 minutes, the solution was concentrated under reduced pressure, and the residue was purified by tin-layer silica gel column chromatography (hexane:ethyl acetate=1:1) to give (E)-2-(tributylstannyl)-3-(3,4-dimethoxyphenyl)acrylamide (14.8 mg, 30%) as a pale yellow oily substance.

Workup

  1. additionwas added
  2. concentrationthe solution was concentrated under reduced pressure
  3. customthe residue was purified by tin-layer silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-a0db5bdf5c1846eaaf6f28f45cf757d7
Source dataset
uspto-grants-2009_09
Patent number
US07595415B2

Reaction notes

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