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Ethyl vinyl ether → 15-Chloro-2-(1-ethoxyethoxy)3-(1-methylethyl)-6,10,14-trimethyl-3,5,9,13-pentadecatetraenenitrile

HRID 892641
Notes
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Reaction equation

HRID 892641 reaction equation
[Cl:1][CH2:2][C:3]([CH3:24])=[CH:4][CH2:5][CH2:6][C:7]([CH3:23])=[CH:8][CH2:9][CH2:10][C:11]([CH3:22])=[CH:12][CH:13]=[C:14]([CH:19]([CH3:21])[CH3:20])[CH:15]([OH:18])[C:16]#[N:17].[CH:25]([O:27][CH2:28][CH3:29])=[CH2:26].C(=O)([O-])O.[Na+].CCCCCC.CCOCC>ClCCl>[Cl:1][CH2:2][C:3]([CH3:24])=[CH:4][CH2:5][CH2:6][C:7]([CH3:23])=[CH:8][CH2:9][CH2:10][C:11]([CH3:22])=[CH:12][CH:13]=[C:14]([CH:19]([CH3:20])[CH3:21])[CH:15]([O:18][CH:25]([O:27][CH2:28][CH3:29])[CH3:26])[C:16]#[N:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8023Ethyl vinyl etherHCID 516892Sodium BicarbonateHCID 21584099Diethylether hexaneHCID 5450637515-Chloro-2-hydroxy-3-(1-methylethyl)-6,10,14-trimethyl-3,5,9,13 pentadecatetraenenitrile

Product 1

HCID 5373709415-Chloro-2-(1-ethoxyethoxy)3-(1-methylethyl)-6,10,14-trimethyl-3,5,9,13-pentadecatetraenenitrileYield 87.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 15-chloro-2-hydroxy-3-(1-methylethyl)-6,10,14-trimethyl-3,5,9,13 pentadecatetraenenitrile (204 mg, 0.56 mmol) prepared in Reference Example 6 and ethyl vinyl ether (100 μl, 0.96 mmol) in dichloromethane (5 ml) is added a very small amount of paratoluenesulfonic acid while stirring under nitrogen atmosphere on an ice-water bath. After 10 minutes, to the mixture are added a saturated aqueous sodium hydrogencarbonate solution (15 ml) and n-hexane/ether (1:1) solution (20 ml) and the organic layer is separated. The aqueous layer is then extracted with n-hexane/ether (1:1) solution (20 ml) for several times. The organic layers are combined and dried over anhydrous sodium sulfate and the solvent is removed by distillation under reduced pressure. The resulting residue is purified by silca gel column chromatography (n-hexane/ethyl acetate =20:1) to give 15-chloro-2-(1-ethoxyethoxy)3-(1-methylethyl)-6,10,14-trimethyl-3,5,9,13-pentadecatetraenenitrile (207 mg, 85%).

Workup

  1. additionis added a very small amount of paratoluenesulfonic acid
  2. customthe organic layer is separated
  3. extractionThe aqueous layer is then extracted with n-hexane/ether (1:1) solution (20 ml) for several times
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent is removed by distillation under reduced pressure
  6. customThe resulting residue is purified by silca gel column chromatography (n-hexane/ethyl acetate =20:1)

Sources & evidence

ORD record
ord-f1d50ab4d198432f890e491bff12e39f
Source dataset
uspto-grants-1992_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05118827

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes