Diethyl Ether → [6-[(6-Bromohexyl)oxy]-1-hexynyl]pyrazine

HRID 1886027Notes

Reaction equation

HRID 1886027 reaction equation
Br[C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.[Br:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]#[CH:21].CCOCC>C(#N)C.[Cu]I>[Br:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]#[C:21][C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 6428002-BromopyrazineHCID 218671586-[(6-Bromohexyl)oxy]-1-hexyne

Product 1

HCID 19876775[6-[(6-Bromohexyl)oxy]-1-hexynyl]pyrazineYield 79.9%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of bromopyrazine (1.64 g), 6-[(6-bromohexyl)oxy]-1-hexyne (2.69 g) N,N-dicyclohexylamine (1.88 g), BTPC (130 mg) and copper (I) iodide (13 mg) in acetonitrile (30 ml) was stirred at 22° under nitrogen for 1 h. Ether (150 ml) was added, the mixture filtered and evaporated in vacuo to an oil which was purified by FCC eluting with hexane-ether (3:2→1:1) followed by ether to give the title compound as a dark yellow oil (2.79 g), t.l.c. (ether) Rf 0.5.

Workup

  1. filtrationthe mixture filtered
  2. customevaporated in vacuo to an oil which
  3. customwas purified by FCC
  4. washeluting with hexane-ether (3:2→1:1)

Sources & evidence

ORD record
ord-b2b7f33de254445cb975718dd2191cfa
Source dataset
uspto-grants-1992_09
Patent number
US05149698

Reaction notes

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