1,2-Dimethoxyethane → HCID 67176666, compound

HRID 43315Notes

Reaction equation

HRID 43315 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1B(O)O)[CH3:2].[OH2:15].[OH-:16].[Li+].CO[CH2:20][CH2:21][O:22][CH3:23]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[CH:6]1[C:7](=[O:15])[CH2:8][CH:3]([CH:1]2[CH2:20][CH2:21][O:22][CH2:23][CH2:2]2)[CH2:4][C:5]1=[O:16])[CH3:2]

Participants

7

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 168937Lithium hydroxide, monohydrateHCID 57437319(2,6-Diethyl-4-methylphenyl)boronic acid

Product 1

HCID 67176666HCID 67176666, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
50 °C

Procedure

A portion of the ylide (0.70 g, 1.76 mmol) prepared in step 5, 2,6-diethyl-4-methylphenylboronic acid (0.372 g, 1.93 mmol), palladium acetate (0.02 g, 0.09 mmol), tetrabutylammonium bromide (0.583 g, 1.76 mmol) and lithium hydroxide monohydrate (0.222 g, 5.28 mmol) are added to a mixture of 1,2-dimethoxyethane (20 ml) and water (5 ml) and the mixture is heated at 50° C. for 5¾ hours. The mixture is cooled to room temperature, filtered through diatomaceous earth to remove the catalyst, and the filtrate is partitioned between ethyl acetate and water. The organic extracts are combined, dried over anhydrous magnesium sulphate, filtered and the filtrate is evaporated in vacuo. The residue is further purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate and hexane to give 2-(2,6-diethyl-4-methylphenyl)-5-(tetrahydropyran-4-yl)cyclohexane-1,3-dione.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. filtrationfiltered through diatomaceous earth
  3. customto remove the catalyst
  4. customthe filtrate is partitioned between ethyl acetate and water
  5. dry with materialdried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. customthe filtrate is evaporated in vacuo
  8. customThe residue is further purified by column chromatography on silica gel
  9. washeluting with a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-4e3a0695360047b4a3a8a916557132ec
Source dataset
uspto-grants-2013_09
Patent number
US08536351B2

Reaction notes

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