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

HRID 1182677Notes

Reaction equation

HRID 1182677 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 (1.77 mL) were added tributyltin hydride (10.3 mL) followed by 1,1′-azobis(cyclohexanecarbonitrile) (378 mg). The mixture was heated for 2.5 h at 80° C., cooled to RT and directly purified by CC (EtOAc/Hept 5:95) to afford the desired compound (5.4 g).

Workup

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

Sources & evidence

ORD record
ord-e7096604ce5643708e747f25fcfa5897
Source dataset
uspto-grants-2014_03
Patent number
US08664203B2

Reaction notes

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