Methyl iodide → 5-(2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl)-3-methoxy-6-methyl-2-cyclohexen-1-one

HRID 1074489Notes

Reaction equation

HRID 1074489 reaction equation
[Li][C:2]([N-]C(C)C)(C)C.[CH2:9]([O:16][C:17]1[CH:22]=[C:21]([C:23]([CH3:31])([CH3:30])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:20]=[CH:19][C:18]=1[CH:32]1[CH2:37][C:36](=[O:38])[CH:35]=[C:34]([O:39][CH3:40])[CH2:33]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CN(C)P(N(C)C)(N(C)C)=O.CI>O1CCCC1>[CH2:9]([O:16][C:17]1[CH:22]=[C:21]([C:23]([CH3:31])([CH3:30])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:20]=[CH:19][C:18]=1[CH:32]1[CH:37]([CH3:2])[C:36](=[O:38])[CH:35]=[C:34]([O:39][CH3:40])[CH2:33]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 12679HexamethylphosphoramideHCID 127882925-(2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl)-3-methoxy-2-cyclohexen-1-oneHCID 178506806HCID 178506806, compound

Product 1

HCID 204968155-(2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl)-3-methoxy-6-methyl-2-cyclohexen-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a -78° C. solution of 0.5 mole of lithiodiisopropylamide in 500 ml of tetrahydrofuran (from 50.5 g, 0.5 mole diisopropylamine and 417 ml of 1.2 M n-butyllithium in hexane) is added dropwise (30 mm) a solution of 217 g (0.5 mole) of 5-(2-benzyloxy-4-(1,1-dimethylheptyl)phenyl)-3-methoxy-2-cyclohexen-1-one in 250 ml of tetrahydrofuran. The reaction is stirred 30 minutes longer at -78° C. followed by the addition of 179 g (1.0 mole) of hexamethylphosphoramide and 78.1 g (0.55 mole) of methyl iodide. The reaction is allowed to slowly warm to room temperature, stirred one hour and quenched by the addition of 10 ml of water. The reaction is evaporated under reduced pressure to remove the tetrahydrofuran and added to one liter ice water-one liter ether. The ether extract is washed with three one liter portions of water, dried over magnesium sulfate and evaporated to yield the title compound in nearly pure form. The title compound is purified via column chromatography on 2 kg of silica gel eluted with ether-pentane.

Workup

  1. temperatureto slowly warm to room temperature
  2. stirringstirred one hour
  3. customquenched by the addition of 10 ml of water
  4. customThe reaction is evaporated under reduced pressure
  5. customto remove the tetrahydrofuran
  6. additionadded to one liter ice water-one liter ether
  7. extractionThe ether extract
  8. washis washed with three one liter portions of water
  9. dry with materialdried over magnesium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-0873741607b44605b1457c9338d8412f
Source dataset
uspto-grants-1983_07
Patent number
US04391827

Reaction notes

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