Methoxymethyl-triphenylphosphonium chloride → 1-[4-(Methoxymethylene)cyclohexyl]-4-[2-(4-propylcyclohexyl)ethyl]-benzene

HRID 1893080Notes

Reaction equation

HRID 1893080 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[CH2:30]([CH:33]1[CH2:38][CH2:37][CH:36]([CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][C:44]([CH:47]3[CH2:52][CH2:51][C:50](=O)[CH2:49][CH2:48]3)=[CH:43][CH:42]=2)[CH2:35][CH2:34]1)[CH2:31][CH3:32]>C1COCC1>[CH3:2][O:3][CH:4]=[C:50]1[CH2:49][CH2:48][CH:47]([C:44]2[CH:43]=[CH:42][C:41]([CH2:40][CH2:39][CH:36]3[CH2:35][CH2:34][CH:33]([CH2:30][CH2:31][CH3:32])[CH2:38][CH2:37]3)=[CH:46][CH:45]=2)[CH2:52][CH2:51]1

Participants

5

Reactant 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxideHCID 584532104-{4-[2-(4-Propylcyclohexyl)ethyl]phenyl}cyclohexanone

Product 1

HCID 584532161-[4-(Methoxymethylene)cyclohexyl]-4-[2-(4-propylcyclohexyl)ethyl]-benzeneYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

THF solution (20 ml) including methoxymethyltriphenylphosphonium chloride (2 g, 5.9 mmol) was slowly added by in solid potassium tert-butoxide (0.6 g, 5.9 mmol) for 3 minutes in a flask filled with argon gas at −10° C. and then stirred for 20 minutes with maintaining the temperature. The temperature of reacting solution was adjusted to 0° C., added slowly dropwise by THF solution (15 ml) of 4-{4-[2-(4-propylcyclohexyl)ethyl]phenyl}cyclohexanone (1.5 g, 4.5 mmol) and then was stirred by warming to a room temperature. After the reaction termination, the resulting solution was diluted by distilled water (20 ml), extracted by ether (20 ml×3 times), washed by distilled water (10 ml×2 times) and then concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate:petroleum ether=1:40) to obtain 1-[4-(methoxymethylene)cyclohexyl]-4-[2-(4-propylcyclohexyl)ethyl]-benzene (1.2 g, 80%).

Workup

  1. additionfilled with argon gas at −10° C.
  2. temperaturewith maintaining the temperature
  3. customwas adjusted to 0° C.
  4. stirringwas stirred
  5. additionAfter the reaction termination, the resulting solution was diluted
  6. distillationby distilled water (20 ml)
  7. extractionextracted by ether (20 ml×3 times)
  8. washwashed
  9. distillationby distilled water (10 ml×2 times)
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by column chromatography (ethyl acetate:petroleum ether=1:40)

Sources & evidence

ORD record
ord-c84242cff309465e9ade98918ea1ec26
Source dataset
uspto-grants-2013_08
Patent number
US08512598B2

Reaction notes

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