Tributylstannane → (E)-2-{tri(n-butyl)stannyl}-3-(4-methoxyphenyl)acrylamide

HRID 736856Notes

Reaction equation

HRID 736856 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([NH2:13])=[O:12])=[CH:5][CH:4]=1.[CH2:14]([SnH:18]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH3:17]>O1CCCC1>[CH2:23]([Sn:18]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:19][CH2:20][CH2:21][CH3:22])/[C:10](=[CH:9]/[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)/[C:11]([NH2:13])=[O:12])[CH2:24][CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 5948TributylstannaneHCID 6979553-(4-Methoxyphenyl)propanamide

Product 1

HCID 11178801(E)-2-{tri(n-butyl)stannyl}-3-(4-methoxyphenyl)acrylamideYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-(4-methoxyphenyl)propionic acid amide (10.3 mg, 0.059 mmol) prepared in Reference Synthetic Example 3 was dissolved in tetrahydrofuran (500 μl) in nitrogen atmosphere, tetrakistriphenylphosphine palladium (1.4 mg, 0.0012 mmol) was added under cooling with ice, and a tetrahydrofuran solution of tri-n-butyltin hydride (20 μl, 0.074 mmol) was dropwise added. After stirring for 10 minutes, the solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to give the desired compound (E)-2-{tri(n-butyl)stannyl}-3-(4-methoxyphenyl)acrylamide (18.6 mg, 68%) as a colorless oily substance.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. concentrationthe solution was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-0465feab14744a1ca8b7ec03e1baf6ee
Source dataset
uspto-grants-2009_09
Patent number
US07595415B2

Reaction notes

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