Tributylstannane → HCID 10992697, compound

HRID 567955Notes

Reaction equation

HRID 567955 reaction equation
C([Cu])#N.C([Li])CCC.[SnH:9]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:11][CH2:12][CH3:13].[H][H].[CH3:24]/[C:25](/[C:29]#[CH:30])=[CH:26]\[CH2:27][OH:28].[NH4+].[OH-].[NH4+].[Cl-]>C1COCC1>[CH2:18]([Sn:9]([CH2:10][CH2:11][CH2:12][CH3:13])([CH2:14][CH2:15][CH2:16][CH3:17])/[CH:30]=[CH:29]/[C:25](/[CH3:24])=[CH:26]/[CH2:27][OH:28])[CH2:19][CH2:20][CH3:21]

Participants

8

Reactant 6

HCID 5948TributylstannaneHCID 53676041-Pentol, (E)-HCID 21863491Ammonium chloride ammonium hydroxideHCID 178418339ButyllithiumHCID 178418361HCID 178418361, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 10992697HCID 10992697, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

CuCN (2.01 g, 22.40 mmol) is introduced into a round-bottomed flask placed under argon, THF (60 ml) is then added and the mixture is cooled to −78° C. n-Butyl-lithium (1.6M, 27.7 ml, 44.40 mmol) is then added dropwise and the mixture is allowed to slowly return to room temperature. It is again cooled to −78° C. and n-Bu3SnH (12 ml, 44.40 mmol) is added and the mixture is stirred for 10 minutes, during which the hydrogen is discharged. (2E)-3-Methylpent-2-en-4-yn-1-ol (1.86 g, 19.31 mmol) is then added, the reaction mixture is left stirring for 45 minutes and then poured into 200 ml of an NH4OH/NH4Cl (10/90) solution. Extraction is carried out with ether (3×100 ml), drying is carried out over Na2SO4 and evaporation is carried out under vacuum.

Workup

  1. additionis then added dropwise
  2. customto slowly return to room temperature
  3. waitthe reaction mixture is left
  4. extractionExtraction
  5. customdrying
  6. customis carried out over Na2SO4 and evaporation

Sources & evidence

ORD record
ord-3706d33b26a64329a2c5fc71af18e273
Source dataset
uspto-grants-2001_01
Patent number
US06180674B2

Reaction notes

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