Tributylstannane → 2-Propen-1-ol, 3-(tributylstannyl)-, (Z)-

HRID 553842Notes

Reaction equation

HRID 553842 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].N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1>>[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 7859Propargyl alcoholHCID 749781,1'-Azobis(cyclohexanecarbonitrile)

Product 1

HCID 714040572-Propen-1-ol, 3-(tributylstannyl)-, (Z)-

Conditions

Temperature
80 °C

Procedure

To neat propargyl alcohol (1 ml) were added tributyl stannane (5.8 ml) followed by 1,1′-azobis(cyclohexanecarbonitrile) (213 mg). The mixture was heated for 2 h at 80° C., cooled to RT, and directly purified by column chromatography (EA/Hept 4/96 to 5/95) to afford 2.98 g of the desired product.

Workup

  1. temperaturecooled to RT
  2. customdirectly purified by column chromatography (EA/Hept 4/96 to 5/95)

Sources & evidence

ORD record
ord-efe40edc487343cb80ac0a3950640812
Source dataset
uspto-grants-2011_11
Patent number
US08048881B2

Reaction notes

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