1,2-Dimethoxyethane → (E)-1-(prop-1-enyl)-4-(3-propylcyclopentyl)cyclohexane

HRID 2358886Notes

Reaction equation

HRID 2358886 reaction equation
CO[CH2:3][CH2:4]OC.C(S(C1N(C2C=CC=CC=2)N=NN=1)(=O)=O)C.[CH2:23]([CH:26]1[CH2:30][CH2:29][CH:28]([CH:31]2[CH2:36][CH2:35][CH:34]([CH:37]=O)[CH2:33][CH2:32]2)[CH2:27]1)[CH2:24][CH3:25].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1COCC1>[CH:37](/[CH:34]1[CH2:35][CH2:36][CH:31]([CH:28]2[CH2:29][CH2:30][CH:26]([CH2:23][CH2:24][CH3:25])[CH2:27]2)[CH2:32][CH2:33]1)=[CH:3]\[CH3:4]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 7536625-Ethylsulfonyl-1-phenyl-1H-tetrazoleHCID 3251421Potassium bis(trimethylsilyl)amide2×HCID 866602914-(3-Propylcyclopentyl)cyclohexanecarboaldehyde

Product 1

HCID 58555698(E)-1-(prop-1-enyl)-4-(3-propylcyclopentyl)cyclohexane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

DME (1,2-dimethoxyethane; 80 ml) and 5-(ethylsulfonyl)-1-phenyl-1H-tetrazole (4.62 g) were added to 4-(3-propylcyclopentyl)cyclohexanecarboaldehyde (3.29 g) obtained in the second step in Example 3, in a reaction vessel under an atmosphere of nitrogen, and the mixture was cooled to −70° C., and then KHMDS (Potassium Hexamethyldisilazide; 20%, in a THF solution) (23.9 ml) was added dropwise. The reaction solution was warmed to room temperature, and was extracted with diethyl ether after the addition of water (50 ml). The resulting organic layer was washed with water and dried over anhydrous sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane= 1/9 by volume) and then purified by means of a preparative HPLC system, Model PLC-561 made by GL Sciences Inc. to give (E)-1-(prop-1-enyl)-4-(3-propylcyclopentyl)cyclohexane (2.0 g).

Workup

  1. customobtained in the second step in Example 3, in a reaction vessel under an atmosphere of nitrogen
  2. temperatureThe reaction solution was warmed to room temperature
  3. extractionwas extracted with diethyl ether
  4. additionafter the addition of water (50 ml)
  5. washThe resulting organic layer was washed with water
  6. dry with materialdried over anhydrous sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane= 1/9 by volume)
  9. custompurified by means of a preparative HPLC system, Model PLC-561

Sources & evidence

ORD record
ord-0326b9d65c264160bcce0f1a113b0493
Source dataset
uspto-grants-2014_04
Patent number
US08685274B2

Reaction notes

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