Tributylstannane → Tributyl(3,3-dimethylbut-1-en-1-yl)stannane

HRID 1478175Notes

Reaction equation

HRID 1478175 reaction equation
[CH2:1]([SnH:5]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[CH3:14][C:15]([CH3:19])([CH3:18])[C:16]#[CH:17]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:10]([Sn:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:6][CH2:7][CH2:8][CH3:9])/[CH:17]=[CH:16]/[C:15]([CH3:19])([CH3:18])[CH3:14])[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 2

HCID 5948TributylstannaneHCID 135123,3-Dimethyl-1-butyne

Product 1

HCID 10948728Tributyl(3,3-dimethylbut-1-en-1-yl)stannane

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Tributyltin hydride (1.637 mL, 6.09 mmol) was added dropwise to a solution of 3,3-dimethylbut-1-yne (500 mg, 6.09 mmol) and Pd(Ph3P)4 (70 mg, 0.06 mmol) in THF (4 mL) at 0° C. in the dark. After 30 minutes of stirring the reaction mixture was warmed to room temperature and was stirred for 16 hours. The solvent was removed under reduced pressure. The crude material was adsorbed onto silica and purification by chromatography eluting with 100% iso-hexane afforded the title compound.

Workup

  1. stirringwas stirred for 16 hours
  2. customThe solvent was removed under reduced pressure
  3. customThe crude material was adsorbed onto silica and purification by chromatography
  4. washeluting with 100% iso-hexane

Sources & evidence

ORD record
ord-c0ea157346164fa89920747ad6865bda
Source dataset
uspto-grants-2016_08
Patent number
US09403810B2

Reaction notes

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