Butyl iodide → 2-Butoxy-7-hydroxymethyl-4-isopropyl-2,4,6-cycloheptatrien-1-one

HRID 234160Notes

Reaction equation

HRID 234160 reaction equation
[OH:1][C:2]1[C:3](=[O:14])[C:4]([CH2:12][OH:13])=[CH:5][CH:6]=[C:7]([CH:9]([CH3:11])[CH3:10])[CH:8]=1.[H-].[Na+].[CH2:17](I)[CH2:18][CH2:19][CH3:20]>CN(C)C=O.ClCCl>[CH2:17]([O:1][C:2]1[C:3](=[O:14])[C:4]([CH2:12][OH:13])=[CH:5][CH:6]=[C:7]([CH:9]([CH3:11])[CH3:10])[CH:8]=1)[CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 3

HCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 178439170HCID 178439170, compound

Product 1

HCID 214599442-Butoxy-7-hydroxymethyl-4-isopropyl-2,4,6-cycloheptatrien-1-oneYield 37.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-hydroxy-7-hydroxymethyl-4-isopropyl-2,4,6-cycloheptatrien-1-one (1.26 g, 6.49 mmol) in dimethylformamide (5 ml) was stirred, and 60% oily sodium hydride (285 mg, 7.13 mmol) was added in small portions to the solution. Subsequently, butyl iodide (1.1 ml, 9.6 mmol) was added and the reaction solution was heated at 80° C. for 4 hours. The solution was diluted with dichloromethane, washed with water and dried over sodium sulfate. Solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography [eluent:hexane/ethyl acetate (1:1)] to give 612 mg of 2-butoxy-7-hydroxymethyl-4-isopropyl-2,4,6-cycloheptatrien-1-one as a yellowish brown oil (yield, 38%).

Workup

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

Sources & evidence

ORD record
ord-602a6df86169440290c1b9a9559a8174
Source dataset
uspto-grants-1997_01
Patent number
US05594144

Reaction notes

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