Iodoethane → 2-Ethoxy-7-hydroxymethyl 4-isopropyl-2,4,6-cycloheptatrien-1-one

HRID 1941150Notes

Reaction equation

HRID 1941150 reaction equation
[H-].[Na+].[OH:3][C:4]1[C:5](=[O:16])[C:6]([CH2:14][OH:15])=[CH:7][CH:8]=[C:9]([CH:11]([CH3:13])[CH3:12])[CH:10]=1.[CH2:17](I)[CH3:18]>CN(C)C=O.ClCCl>[CH2:17]([O:3][C:4]1[C:5](=[O:16])[C:6]([CH2:14][OH:15])=[CH:7][CH:8]=[C:9]([CH:11]([CH3:13])[CH3:12])[CH:10]=1)[CH3:18]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178439170HCID 178439170, compound

Product 1

HCID 214599402-Ethoxy-7-hydroxymethyl 4-isopropyl-2,4,6-cycloheptatrien-1-oneYield 76%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

60% oily sodium hydride (256 mg, 6.4 mmol) was added to a solution of 2-hydroxy-7-hydroxymethyl-4-isopropyl-2,4,6-cycloheptatrien-1-one (1.13 g, 5.82 mmol) in dimethylformamide (5 ml) with stirring. Then, ethyl iodide (0.7 ml, 8.75 mmol) was added and the reaction mixture was heated at 70° C. for 3 hours. The reaction solution was diluted with dichloromethane, washed with water, and dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography [eluent: hexane/ethyl acetate (2:3)] to give 485 mg of 2-ethoxy-7-hydroxymethyl-4-isopropyl-2,4,6-cycloheptatrien-1-one as a pale yellow amorphous powder (yield: 76%).

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. distillationAfter the solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography [eluent: hexane/ethyl acetate (2:3)]

Sources & evidence

ORD record
ord-81dd237222ca4c279cac754748229011
Source dataset
uspto-grants-1997_12
Patent number
US05703071

Reaction notes

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