Dimethylformamide → (E,E)-N-methyl-N-(6,6-dimethyl-2-hepten-4-ynyl)-3-(4-chloro-2-butenyloxy)benzylamine

HRID 1464751Notes

Reaction equation

HRID 1464751 reaction equation
[CH3:1][N:2]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=1)[CH2:3]/[CH:4]=[CH:5]/[C:6]#[C:7][C:8]([CH3:11])([CH3:10])[CH3:9].[H-].[Na+].CN(C)C=O.[Cl:27][CH2:28]/[CH:29]=[CH:30]/[CH2:31]Cl>O1CCCC1>[CH3:1][N:2]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:31]/[CH:30]=[CH:29]/[CH2:28][Cl:27])[CH:14]=1)[CH2:3]/[CH:4]=[CH:5]/[C:6]#[C:7][C:8]([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 6421971,4-Dichloro-2-butene, (2E)-HCID 19916986(E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-3-hydroxybenzylamine

Product 1

HCID 19916973(E,E)-N-methyl-N-(6,6-dimethyl-2-hepten-4-ynyl)-3-(4-chloro-2-butenyloxy)benzylamineYield 65.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

245 mg of (E)-N-methyl-N-(6,6-dimethyl-2-hepten-4-ynyl)-3-hydroxybenzylamine was dissolved in 5 ml of tetrahydrofuran, and under ice cooling, 40 mg of oily sodium hydride was added. After the mixture was stirred for 15 minutes, a dimethylformamide solution (3ml) of 125 mg of (E)-1,4-dichloro-2-butene was added. The mixture was stirred at room temperature for 12 hours, and then the solvent was evaporated. The residue was worked up in a customary manner, and purified by silica gel column chromatography [hexane/ethyl acetate=5/1] to give 216 mg of the captioned compound as a colorless oil.

Workup

  1. stirringThe mixture was stirred at room temperature for 12 hours
  2. customthe solvent was evaporated
  3. custompurified by silica gel column chromatography [hexane/ethyl acetate=5/1]

Sources & evidence

ORD record
ord-db628ae138be425fb18f1cb484614588
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

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