Hydrochloric Acid → 2-(2,6-Diethyl-4-methylphenyl)-5-([1,3]dioxolan-2-ylmethyl)cyclohexane-1,3-dione

HRID 1027369

Reaction equation

HRID 1027369 reaction equation
[IH2+].[CH2:2]([C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH2:11][CH3:12])[C:5]=1B(O)O)[CH3:3].[OH2:16].[OH-:17].[Li+].Cl.C[O:21][CH2:22][CH2:23][O:24][CH3:25]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:2]([C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH2:11][CH3:12])[C:5]=1[CH:7]1[C:8](=[O:16])[CH2:9][CH:4]([CH2:2][CH:25]2[O:21][CH2:22][CH2:23][O:24]2)[CH2:5][C:6]1=[O:17])[CH3:3]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 80711,2-DimethoxyethaneHCID 168937Lithium hydroxide, monohydrateHCID 3715291Iodine, ion (I1+)HCID 57437319(2,6-Diethyl-4-methylphenyl)boronic acid

Product 1

HCID 667251072-(2,6-Diethyl-4-methylphenyl)-5-([1,3]dioxolan-2-ylmethyl)cyclohexane-1,3-dione

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

The iodonium ylide (477 mg, 1.19 mmol) prepared in Step 3a is added to a mixture of 2,6-diethyl-4-methylphenylboronic acid (343 mg, 1.79 mmol), tetrabutylammonium bromide (385 mg, 1.19 mmol), lithium hydroxide monohydrate (151 mg, 3.57 mmol) and palladium (II) acetate (13 mgs) in a mixture of 1,2-dimethoxyethane (10.8 ml) and water (2.7 ml) and the reaction mixture is heated at 55° C. for 5 hours. The reaction is then cooled, dilute aqueous hydrochloric acid is added, and the mixture is extracted with ethyl acetate. The organic extracts are combined, washed with water, dried over anhydrous magnesium sulfate, filtered and the filtrate is concentrated in vacuo. The residue is purified by column chromatography on silica gel to give 2-(2,6-diethyl-4-methylphenyl)-5-([1,3]dioxolan-2-ylmethyl)cyclohexane-1,3-dione

Workup

  1. temperatureThe reaction is then cooled
  2. extractionthe mixture is extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated in vacuo
  7. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-092fb6cee83243338803759582fbd833
Source dataset
uspto-grants-2014_05
Patent number
US08735322B2

Linked notes

Loading…