Benzyl Chloride → 2-Benzyloxy-7-hydroxymethyl-4-isopropyl-2,4,6-cycloheptatrien-1-one

HRID 234161Notes

Reaction equation

HRID 234161 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](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>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)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 178439170HCID 178439170, compound

Product 1

HCID 214599532-Benzyloxy-7-hydroxymethyl-4-isopropyl-2,4,6-cycloheptatrien-1-oneYield 43.3%

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 (1.15 g, 5.92 mmol) in dimethylformamide (5 ml) was stirred while 60% oily sodium hydride (260 mg, 6.50 mmol) was gradually added thereto. Subsequently, benzyl chloride (1 ml, 8.41 mmol) was added, then the reaction solution was heated at 80° C. for 4 hours. The reaction 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 729 mg of 2-benzyloxy-7-hydroxymethyl-4-isopropyl-2,4,6-cycloheptatrien-1-one (yield: 43%) as a pale yellowish brown oil.

Workup

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

Sources & evidence

ORD record
ord-d952dc83583341dbb3427bfc7d512468
Source dataset
uspto-grants-1997_01
Patent number
US05594144

Reaction notes

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