Tributylstannane → (E)-3-(tributylstannyl)prop-2-en-1-ol

HRID 1587015Notes

Reaction equation

HRID 1587015 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].[CH2:5]([SnH:9]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH3:8]>C1(C)C=CC=CC=1>[CH2:14]([Sn:9]([CH2:5][CH2:6][CH2:7][CH3:8])([CH2:10][CH2:11][CH2:12][CH3:13])/[CH:3]=[CH:2]/[CH2:1][OH:4])[CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 5948TributylstannaneHCID 7859Propargyl alcohol

Product 1

HCID 10043273(E)-3-(tributylstannyl)prop-2-en-1-ol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of propargyl alcohol (2.24 g) and α,α'-azoisobutyronitrile (0.10 g) in anhydrous toluene (150 ml) is added tributyltin hydride (12.9 ml) and the mixture heated at reflux for about 2.5 hours, cooled and concentrated in vacuo. The crude product is purified by flash chromatography in 15% ether in hexane to give the desired product.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for about 2.5 hours
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by flash chromatography in 15% ether in hexane

Sources & evidence

ORD record
ord-96f7297063ff4536a13820f86abb994a
Source dataset
uspto-grants-1993_06
Patent number
US05216015

Reaction notes

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