Isovaleryl chloride → 2-Methyldec-5-yn-4-one

HRID 602240Notes

Reaction equation

HRID 602240 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5](Cl)(=[O:10])[CH2:6][CH:7]([CH3:9])[CH3:8].C[Si]([C:16]#[C:17][CH2:18][CH2:19][CH2:20][CH3:21])(C)C>C(Cl)(Cl)(Cl)Cl>[CH3:8][CH:7]([CH2:6][C:5](=[O:10])[C:16]#[C:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH3:9]

Participants

5

Reactant 3

HCID 66054Isovaleryl chlorideHCID 5869591-Trimethylsilyl-1-hexyneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 713733612-Methyldec-5-yn-4-oneYield 100.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent3×

Conditions

Temperature
2 °C

Procedure

21.6 g of AlCl3 (0.162 moles) in 65 mL of CCl4 are cooled to 2° C. and 19.7 mL of isovaleroyl chloride (0.162 moles) in 30 mL of CCl4 are added dropwise. 25 g of trimethylsilylhexyne (0.162 moles) in 30 mL of CCl4 are then added dropwise. The mixture is stirred for 1 h at 2° C. and for 24 h at ambient temperature. It is poured into 200 mL of 1:3 37% HCl/ice, stirred for 1 h, the phases are separated and the aqueous phase is extracted with CH2Cl2. The combined organic phases are washed to neutrality, dried with Na2SO4 and evaporated. 27 g of product are obtained, which are used in the subsequent step without further purification. Formula: C11H18O (m.w. 166.27). Quantitative yield. IR (film) 2956; 2209; 1670 cm−1.

Workup

  1. stirringstirred for 1 h
  2. customthe phases are separated
  3. extractionthe aqueous phase is extracted with CH2Cl2
  4. washThe combined organic phases are washed to neutrality
  5. dry with materialdried with Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-d1b3284b1a1941ca8a06f16d326d416b
Source dataset
uspto-grants-2011_03
Patent number
US07906501B2

Reaction notes

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