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

HRID 1258366Notes

Reaction equation

HRID 1258366 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].CC(N=NC(C#N)(C)C)(C#N)C>>[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 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 7859Propargyl alcohol

Product 1

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

Conditions

Temperature
80 °C

Procedure

To neat propargyl alcohol (5 ml) were added tributyltin hydride (29.2 ml) followed by AIBN (716 mg). The mixture was heated for 2.75 h at 80° C., cooled to RT and directly purified by CC (EA/Hept 5/95) to afford the desired compound (12.9 g).

Workup

  1. temperaturecooled to RT
  2. customdirectly purified by CC (EA/Hept 5/95)

Sources & evidence

ORD record
ord-b676fd4be60d4fe29784cb4f17e1530d
Source dataset
uspto-grants-2013_06
Patent number
US08466156B2

Reaction notes

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