Diethyl Ether → HCID 12641422, compound

HRID 2422011Notes

Reaction equation

HRID 2422011 reaction equation
[C:1]1([CH3:12])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[CH2:9][CH:10]=[O:11].C[Mg+].[Br-].[CH3:16]COCC>C1COCC1>[C:3]1([CH3:8])[CH:4]=[C:5]([CH3:7])[CH:6]=[C:1]([CH3:12])[C:2]=1[CH2:9][CH:10]([OH:11])[CH3:16]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 3003822-(2,4,6-Trimethylphenyl)acetaldehydeHCID 178418689HCID 178418689, compound

Product 1

HCID 12641422HCID 12641422, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Mesitylacetaldehyde (0.68 g, 4.19 mmol) was dissolved in THF (5.0 mL, dry) and MeMgBr in Et2O (3.0M, 0.75 g, 6.29 mmol)) was added slowly at 0° C. The cooling bath was removed and the reaction mixture was stirred at rt for 4.5 h. The mixture was cooled to 0° C. and excess Grignard reagent was hydrolyzed with HCl (1N). The mixture was diluted with water and extracted with Et2O. The organic layer was dried over Na2SO4, evaporated and the residue was purified by column chromatography on silica gel using MTBE, heptane and DCM as eluant giving the title compound (0.51 g, 61%). 1H NMR (CDCl3, 500 MHz) δ 6.88-6.85 (m, 2H), 4.08-3.99 (m, 1H), 2.87-2.72 (m, 2H), 2.32 (s, 6H), 2.26 (s, 3H), 1.29 (d, 3H).

Workup

  1. customThe cooling bath was removed
  2. temperatureThe mixture was cooled to 0° C.
  3. additionThe mixture was diluted with water
  4. extractionextracted with Et2O
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customevaporated
  7. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-931356e574354a9da4ba8cc8c2c01600
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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