Valeryl chloride → 1-Heptyn-3-one, 1-(trimethylsilyl)-

HRID 1413569Notes

Reaction equation

HRID 1413569 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[CH3:8][Si:9]([C:12]#[C:13][Si](C)(C)C)([CH3:11])[CH3:10].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[CH3:8][Si:9]([C:12]#[C:13][C:1]([CH2:2][CH2:3][CH2:4][CH3:5])=[O:6])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 61186Valeryl chlorideHCID 84564Bis(trimethylsilyl)acetyleneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 110195111-Heptyn-3-one, 1-(trimethylsilyl)-Yield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 14.4 grams of valeryl chloride and 20.4 grams of bis-trimethylsilylacetylene in 300 ml of dry methylene chloride, cooled in an ice bath, is added powdered anhydrous aluminum chloride, portionwise, over a period of 20 minutes. The mixture is stirred for 5 minutes, then the cooling bath is removed and the mixture stirred at room temperature for 4 hours. The mixture is poured into 500 ml of ice-water. The organic layer is separated, washed with water and brine, dried over anhydrous sodium sulfate and filtered through diatomaceous earth. The mother liquor is evaporated to dryness giving a brownish residue. The residue is Kugelrohr-distilled to give 16.56 grams of colorless liquid at 45° C./0.3 mm which is essentially identical with the authentic product.

Workup

  1. additionis added
  2. customthe cooling bath is removed
  3. stirringthe mixture stirred at room temperature for 4 hours
  4. additionThe mixture is poured into 500 ml of ice-water
  5. customThe organic layer is separated
  6. washwashed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered through diatomaceous earth
  9. customThe mother liquor is evaporated to dryness
  10. customgiving a brownish residue
  11. distillationThe residue is Kugelrohr-distilled

Sources & evidence

ORD record
ord-7759eb5a5b5b4d129735e5fca5f49ff3
Source dataset
uspto-grants-1981_02
Patent number
US04250325

Reaction notes

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