Nonanoyl chloride → 1-(Trimethylsilyl)undec-1-yn-3-one

HRID 1722337Notes

Reaction equation

HRID 1722337 reaction equation
[C:1](Cl)(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[CH3:12][Si:13]([C:16]#[C:17][Si](C)(C)C)([CH3:15])[CH3:14].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[CH3:12][Si:13]([CH3:15])([CH3:14])[C:16]#[C:17][C:1](=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 69819Nonanoyl chlorideHCID 84564Bis(trimethylsilyl)acetyleneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 147984691-(Trimethylsilyl)undec-1-yn-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 500ml of CH2Cl2 was added 53ml (294 mmol) of nonanoyl chloride and 50g (293.4 mmol) of bis(trimethylsilyl) acetylene. The reaction mixture was cooled in an ice bath and 40g (300 mmol) of AlCl3 was added portionwise with stirring over 1/2 hour. After stirring for an additional hour, the reaction mixture was quenched with ice. Water was added to the reaction mixture and it was extracted 3x with 200ml aliquots of diethyl ether. The combined extracts were washed 2x with 50ml aliquots of saturated NaHCO3, 1 x with brine, and then dried (MgSO4). The solvent was removed in vacuo to give a brown oil which was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. stirringAfter stirring for an additional hour
  3. customthe reaction mixture was quenched with ice
  4. additionWater was added to the reaction mixture and it
  5. extractionwas extracted 3x with 200ml aliquots of diethyl ether
  6. washThe combined extracts were washed 2x with 50ml aliquots of saturated NaHCO3, 1 x with brine
  7. dry with materialdried (MgSO4)
  8. customThe solvent was removed in vacuo
  9. customto give a brown oil which
  10. customwas used without further purification

Sources & evidence

ORD record
ord-3f5794535b584172970ae63906996926
Source dataset
uspto-grants-1989_08
Patent number
US04855324

Reaction notes

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