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

HRID 1896155Notes

Reaction equation

HRID 1896155 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 10043273(E)-3-(tributylstannyl)prop-2-en-1-ol

Conditions

Temperature
80 °C

Procedure

To neat propargyl alcohol (1 mL) were added tributyltin hydride (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 CC (EA/Hept 4/96 to 5/95) to afford the desired compound (2.98 g).

Workup

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

Sources & evidence

ORD record
ord-d7b9438fc9d24730af13ae47dbe284a0
Source dataset
uspto-grants-2013_08
Patent number
US08518912B2

Reaction notes

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