HCID 20572046, compound → HCID 57131341, compound

HRID 1577292Notes

Reaction equation

HRID 1577292 reaction equation
[CH2:1]([Li])[CH3:2].Br[CH2:5][C:6]([CH3:14])([CH3:13])[CH2:7][C:8]([CH3:12])([CH3:11])[C:9]#[N:10]>CCOCC>[CH3:5][C:6]1([CH3:14])[CH2:7][C:8]([CH3:12])([CH3:11])[CH2:9][N:10]=[C:13]1[CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 20572046HCID 20572046, compoundHCID 178506846HCID 178506846, compound

Product 1

HCID 57131341HCID 57131341, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

0.1 mol of ethyl lithium dissolved in 200 ml of anhydrous ether is added drop by drop in an inert atmosphere to 22 g of 5-bromo-2,2,4,4-tetramethyl-pentane nitrile in 60 ml of anhydrous ether. This reaction medium is maintained between 0° and 5° C. during the addition and then for an additional 30 minutes and then is kept at room temperature for 4 hours. After hydrolysis, the aqueous phase is extracted with ether. The 3,3,5,5 tetramethyl-2-ethyl-3,4,5,6-tetrahydropyridine is then isolated by distillation. A colorless liquid of B.P.2.10 -2=40° C. is obtained in a yield of 40%.

Workup

  1. temperatureThis reaction medium is maintained between 0° and 5° C. during the addition
  2. waitis kept at room temperature for 4 hours
  3. customAfter hydrolysis
  4. extractionthe aqueous phase is extracted with ether

Sources & evidence

ORD record
ord-8b5452586cfb49cbbe2f47ca821792e1
Source dataset
uspto-grants-1981_09
Patent number
US04287337

Reaction notes

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