Iodoethane → HCID 58951764, compound

HRID 1694812Notes

Reaction equation

HRID 1694812 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].I[CH2:15][CH3:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)C>[CH2:15]([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)[CH3:16]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 54206997HCID 54206997, compound

Product 1

HCID 58951764HCID 58951764, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 0.30 g (1.68 mmol) 2,6-diethyl-4-hydroxy-benzaldehyde in 8 ml N,N-dimethylformamide in a pressure tube were added 0.16 ml (2.02 mmol) iodoethane and 0.35 g (2.52 mmol) potassium carbonate. The tube was sealed and the reaction mixture was heated at 50° C. for 16 h. The reaction mixture was then cooled to room temperature, diluted with diethyl ether, and washed sequentially with water and 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 1:30) to afford 0.31 g (88%) of the title compound as a yellow oil. MS (ISP): 207.3 ([M+H]+).

Workup

  1. customThe tube was sealed
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. washwashed sequentially with water and 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 1:30)

Sources & evidence

ORD record
ord-56723dfb5b4948d097d1a300410b6bdd
Source dataset
uspto-grants-2012_04
Patent number
US08158668B2

Reaction notes

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