Methoxymethyl-triphenylphosphonium chloride → HCID 178494964, compound

HRID 1463745Notes

Reaction equation

HRID 1463745 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:24]([C@H:26]1[CH2:31][CH2:30][C@H:29]([C@H:32]2[CH2:37][CH2:36][C@H:35]([CH2:38][CH2:39][CH:40]=O)[CH2:34][CH2:33]2)[CH2:28][CH2:27]1)#[N:25]>COC(C)(C)C.O>[CH3:2][O:3][CH:4]=[CH:40][CH2:39][CH2:38][C@H:35]1[CH2:34][CH2:33][C@H:32]([C@H:29]2[CH2:28][CH2:27][C@H:26]([C:24]#[N:25])[CH2:31][CH2:30]2)[CH2:37][CH2:36]1

Participants

5

Reactant 2

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 178511239HCID 178511239, compound

Product 1

HCID 178494964HCID 178494964, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent2×

Procedure

4.11 g of methoxymethyl-triphenylphosphonium chloride were suspended in 60 ml of tert.butyl methyl ether while gassing with argon and treated at room temperature within 2 minutes with 1.26 g of potassium tert.butylate. The suspension was stirred at room temperature for a further 1 hour, then cooled to 0° C. and treated dropwise within 5 minutes with a solution of 1.98 g of 3-[trans-4-(trans-4-cyanocyclohexyl)cyclohexyl]propionaldehyde in 25 ml of tert.butyl methyl ether. The reaction mixture was stirred at 0° C. for a further 45 minutes, then diluted with 100 ml of water and extracted three times with 100 ml of diethyl ether each time. The organic phases were washed twice with 100 ml of water each time, dried over magnesium sulfate, filtered and concentrated. Chromatographic purification of the crude product (5.1 g) on silica gel at 0.5 bar with ethyl acetate/petroleum ether (vol. 5:95) gave 2.0 g of trans-4-[trans-4-(4-methoxy-3-butenyl)cyclohexyl)cyclohexanecarbonitrile as a colorless milky oil.

Workup

  1. temperaturecooled to 0° C.
  2. stirringThe reaction mixture was stirred at 0° C. for a further 45 minutes
  3. extractionextracted three times with 100 ml of diethyl ether each time
  4. washThe organic phases were washed twice with 100 ml of water each time
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customChromatographic purification of the crude product (5.1 g) on silica gel at 0.5 bar with ethyl acetate/petroleum ether (vol. 5:95)

Sources & evidence

ORD record
ord-370dd276f98541deaac9aedfbf1e348a
Source dataset
uspto-grants-1994_04
Patent number
US05302317

Reaction notes

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