3-Ethoxycyclohex-2-ene-1-one → 3-[2-Benzyloxy-4-(1,1-Dimethylheptyl)phenyl]cyclohex-2-enone

HRID 1762249Notes

Reaction equation

HRID 1762249 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:16]([CH3:24])([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH3:17])[CH:12]=[CH:13][C:14]=1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].C([O:28][C:29]1[CH2:34][CH2:33][CH2:32][C:31](=O)[CH:30]=1)C>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:16]([CH3:24])([CH3:17])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:12]=[CH:13][C:14]=1[C:31]1[CH2:32][CH2:33][CH2:34][C:29](=[O:28])[CH:30]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 792163-Ethoxycyclohex-2-ene-1-oneHCID 5462224MagnesiumHCID 128821642-(Benzyloxy)-1-bromo-4-(2-methyloctan-2-YL)benzene

Product 1

HCID 198553803-[2-Benzyloxy-4-(1,1-Dimethylheptyl)phenyl]cyclohex-2-enoneYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 3.89 g. (10 mmoles) of 2-(3-benzyloxy-4-bromophenyl)-2-methyloctane in 10 ml. of tetrahydrofuran was slowly added to 360 ml. (14.4 mmoles) of 70-80 mesh magnesium metal. The resulting mixture was refluxed for 30 minutes and then cooled to 0° C. To this solution was slowly added a solution of 1.40 g. (10 mmoles) of 3-ethoxy-2-cyclohexen-1-one in 3 ml. of tetrahydrofuran. The reaction mixture was stirred for 30 minutes at 0° C. and then quenched by the addition of 20 ml. of 1N sulfuric acid and heating on the steam bath for 30 minutes. It was then cooled and added to 200 ml. of ether--200 ml. of water. The organic extract was washed successively with 200 ml. of saturated sodium bicarbonate and 200 ml. of saturated sodium chloride, dried over magnesium sulfate and evaporated to an oil. The crude product was purified via column chromatography on 170 g. of silica gel eluted with 1:1 ether:pentane to yield 2.5 g. (54%) of the title compound as and oil.

Workup

  1. temperatureThe resulting mixture was refluxed for 30 minutes
  2. additionTo this solution was slowly added a solution of 1.40 g
  3. customquenched by the addition of 20 ml
  4. temperatureof 1N sulfuric acid and heating on the steam bath for 30 minutes
  5. temperatureIt was then cooled
  6. additionadded to 200 ml
  7. extractionThe organic extract
  8. washwas washed successively with 200 ml
  9. dry with materialof saturated sodium chloride, dried over magnesium sulfate
  10. customevaporated to an oil
  11. customThe crude product was purified via column chromatography on 170 g
  12. washof silica gel eluted with 1:1 ether
  13. custompentane to yield 2.5 g

Sources & evidence

ORD record
ord-cac19bddda4b400aa2474a9a343d0d29
Source dataset
uspto-grants-1989_05
Patent number
US04831059

Reaction notes

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