Methanol → Acetic acid 5,5-dimethyl-4-oxo-hex-2-ynyl ester

HRID 553840Notes

Reaction equation

HRID 553840 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[C:8]([O:11][CH2:12][C:13]#[CH:14])(=[O:10])[CH3:9].[I-].CO>CCN(CC)CC.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:3][C:2]([CH3:5])([CH3:4])[C:1](=[O:6])[C:14]#[C:13][CH2:12][O:11][C:8](=[O:10])[CH3:9]

Participants

7

Reactant 4

HCID 887MethanolHCID 30165Iodide IonHCID 62493Pivaloyl chlorideHCID 69388Propargyl acetate

Product 1

HCID 86622407Acetic acid 5,5-dimethyl-4-oxo-hex-2-ynyl ester

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

Pivaloyl chloride (612 μl), propargyl acetate (644 μl), cupper iodide (12 mg) and bis-(triphenylphosphine) palladium(II)-dichloride (9.1 mg) in NEt3 (10 ml) were stirred at RT for 24 h. MeOH was added and the mixture was evaporated off. The residue was taken up in Et2O and the resulting suspension filtered off. The solution was washed with a 1M HCl solution, water, dried (Na2SO4) and evaporated off. Column chromatography (EA/Hept 1/3) afforded 343 mg of the desired compound.

Workup

  1. customthe mixture was evaporated off
  2. filtrationthe resulting suspension filtered off
  3. washThe solution was washed with a 1M HCl solution, water
  4. dry with materialdried (Na2SO4)
  5. customevaporated off

Sources & evidence

ORD record
ord-6b7e575f8c374d0e97c52bfcfcb28645
Source dataset
uspto-grants-2011_11
Patent number
US08048881B2

Reaction notes

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