Diethyl Ether → HCID 58951764, compound

HRID 254590Notes

Reaction equation

HRID 254590 reaction equation
[CH2:1]([C:3]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([CH2:12][CH3:13])[C:4]=1[CH:5]=[O:6])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].IC.[CH3:22][CH2:23]OCC>CN(C)C=O>[CH2:22]([O:11][C:9]1[CH:8]=[C:7]([CH2:12][CH3:13])[C:4]([CH:5]=[O:6])=[C:3]([CH2:1][CH3:2])[CH:10]=1)[CH3:23]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 54206997HCID 54206997, compound

Product 1

HCID 58951764HCID 58951764, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1.10 g (5.92 mmol)) 2,6-diethyl-4-hydroxy-benzaldehyde in 15 ml N,N-dimethylformamide in a pressure tube were added 4.83 g (14.8 mmol) cesium carbonate and 1.05 ml (13.0 mmol) iodomethane. The tube was sealed and the reaction mixture was heated at 60° C. for 16 h. The reaction mixture was cooled to room temperature, diluted with ether, and washed with saturated brine. The phases were separated and the organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, ethyl acetate/heptane gradient) to afford 1.00 g (82%) of the title compound as a yellow oil. 1H-NMR (CDCl3): 1.25 (6H, t, 2×CH3), 1.44 (3H, t, CH3), 2.98 (4H, q, 2×CH2), 4.10 (2H, q, OCH2), 6.62 (2H, s, 2×ArH), 10.45 (1H, s, CH═O).

Workup

  1. customThe tube was sealed
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washwashed with saturated brine
  4. customThe phases were separated
  5. dry with materialthe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (silica gel, ethyl acetate/heptane gradient)

Sources & evidence

ORD record
ord-041c0f3895cd4e5d941e0b2533822d74
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Reaction notes

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