1,3-Dibromopropane → 3-Bromopropoxy-7-hydroxymethyl 4-isopropyl-2,4,6-cycloheptatrien-1-one

HRID 1941154Notes

Reaction equation

HRID 1941154 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.[Br:17][CH2:18][CH2:19][CH2:20]Br>CN(C)C=O.ClCCl>[Br:17][CH2:18][CH2:19][CH2:20][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

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 178439170HCID 178439170, compound

Product 1

HCID 214599293-Bromopropoxy-7-hydroxymethyl 4-isopropyl-2,4,6-cycloheptatrien-1-oneYield 14%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

60% oily sodium hydride (292, mg, 7.3 mmol) in small portions were added to a solution of 2-hydroxy-7-hydroxymethyl-4-isopropyl-2,4,6-cycloheptatrien-1-one (1.29 g, 6.64 mmol) in dimethylformamide (5 ml) with stirring. After addition of 1,3-dibromopropane (1.35 ml, 13.3 mmol), the solution was heated at 80° C. for 4 hours. The solution was diluted with dichloromethane, washed with water, and dried over sodium sulfate. After solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography [eluent: hexane/ethyl acetate (1:1)] to give 293 mg of 2-(3-bromopropoxy)-7-hydroxymethyl-4-isopropyl-2,4,6-cycloheptatrien-1-one as a pale yellow crystal (yield: 14%).

Workup

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

Sources & evidence

ORD record
ord-5412fd77d9ae4076bc15c24b1034d784
Source dataset
uspto-grants-1997_12
Patent number
US05703071

Reaction notes

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