Ammonium Chloride → 1-(1-Ethoxyethoxy)-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraene-1-carbonitrile

HRID 486868Notes

Reaction equation

HRID 486868 reaction equation
Cl[CH2:2][C:3]([CH3:29])=[CH:4][CH2:5][CH2:6][C:7]([CH3:28])=[CH:8][CH2:9][CH2:10][C:11]([CH3:27])=[CH:12][CH:13]=[C:14]([CH:24]([CH3:26])[CH3:25])[CH:15]([O:18][CH:19]([O:21][CH2:22][CH3:23])[CH3:20])[C:16]#[N:17].[Cl-].[NH4+]>CCCCCC.C1C=CC=CC=1.C1C=CC=CC=1>[CH2:22]([O:21][CH:19]([O:18][C:15]1([C:16]#[N:17])[CH2:2][C:3]([CH3:29])=[CH:4][CH2:5][CH2:6][C:7]([CH3:28])=[CH:8][CH2:9][CH2:10][C:11]([CH3:27])=[CH:12][CH:13]=[C:14]1[CH:24]([CH3:26])[CH3:25])[CH3:20])[CH3:23]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 5373709415-Chloro-2-(1-ethoxyethoxy)3-(1-methylethyl)-6,10,14-trimethyl-3,5,9,13-pentadecatetraenenitrile

Product 1

HCID 538231811-(1-Ethoxyethoxy)-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-cyclotetradecatetraene-1-carbonitrileYield 51.5%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 110624Benzene hexaneSolvent

Procedure

A solution of hexamethyldisilazane lithium amide (205 mg, 1.11 mmol) in dry hexane/benzene (1:4) solution (5 ml) is stirred on an oil bath at 90° C. and thereto is dropwise added a solution of cyanohydrin ethoxyethyl ether which is 15-chloro-2-(1-ethoxyethoxy)-3-(1-methylethyl)-6, 10,14-trimethyl-3,5,9,13-pentadecatetraenenitrile (115 mg, 0.26 mmol) in dry benzene (6 ml) over 20 minutes. After stirring the mixture at this temperature for 5 minutes, a saturated aqueous ammonium chloride solution is added while stirring on an ice-water bath. The organic layer is extracted with ether (20 ml ×2) and the solvent is removed by distillation under reduced pressure to give 1-(1-ethoxyethoxy)-2-(1-methylethyl)-5,9,13-trimethyl-2,4, 8,12-cyclotetradecatetraene-1-carbonitrile (51.6 mg, 50%) as a mixture of diastereomers. This product is subjected to silica gel column chromatography (n-hexane/ether=20:1) to give one isomer of the above formula.

Workup

  1. customover 20 minutes
  2. stirringwhile stirring on an ice-water bath
  3. extractionThe organic layer is extracted with ether (20 ml ×2)
  4. customthe solvent is removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-9f04901323d64b759b6f08d41e25b1f9
Source dataset
uspto-grants-1994_03
Patent number
US05292911

Reaction notes

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