Sodium Chloride → 2-(1-Methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraene-1-carbonitrile

HRID 486869Notes

Reaction equation

HRID 486869 reaction equation
C(OC(O[C:7]1([C:27]#[N:28])[CH2:20][C:19]([CH3:21])=[CH:18][CH2:17][CH2:16][C:15]([CH3:22])=[CH:14][CH2:13][CH2:12][C:11]([CH3:23])=[CH:10][CH:9]=[C:8]1[CH:24]([CH3:26])[CH3:25])C)C.[Cl-].[Na+]>CO>[CH3:26][CH:24]([C:8]1[CH:7]([C:27]#[N:28])[CH2:20][C:19]([CH3:21])=[CH:18][CH2:17][CH2:16][C:15]([CH3:22])=[CH:14][CH2:13][CH2:12][C:11]([CH3:23])=[CH:10][CH:9]=1)[CH3:25]

Participants

4

Reactant 2

HCID 5234Sodium ChlorideHCID 538231811-(1-Ethoxyethoxy)-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraene-1-carbonitrile

Product 1

HCID 543163162-(1-Methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraene-1-carbonitrileYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-(1-ethoxyethoxy)-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraene -1-carbonitrile (31.8 mg, 0.08 mmol) prepared in Example 1 in methanol (3 ml) is stirred on an ice-water bath and thereto is added a very small amount of paratoluenesulfonic acid. After stirring the mixture at this temperature for 1 hour, a saturated aqueous sodium chloride solution (3 ml) is added and the mixture is extracted with ether (10 ml ×2). The solvent is removed by distillation under reduced pressure and the resulting residue is purified by silica gel column chromatography (n-hexane/ethyl acetate=7:1) to give 2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraene-1-carbonitrile (13.7 mg, 60%).

Workup

  1. additionis added a very small amount of paratoluenesulfonic acid
  2. extractionthe mixture is extracted with ether (10 ml ×2)
  3. customThe solvent is removed by distillation under reduced pressure
  4. customthe resulting residue is purified by silica gel column chromatography (n-hexane/ethyl acetate=7:1)

Sources & evidence

ORD record
ord-bd527516ccaa4db5bb8ec30b416e381b
Source dataset
uspto-grants-1994_03
Patent number
US05292911

Reaction notes

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