Diethyl Ether → HCID 18186821, compound

HRID 1296629Notes

Reaction equation

HRID 1296629 reaction equation
[C:1]1([CH:7]([OH:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:10][C:11]1[CH:16]=[N:15][CH:14]=[C:13](Cl)[N:12]=1.CCOCC>O1CCOCC1>[Cl:10][C:11]1[CH:16]=[N:15][CH:14]=[C:13]([O:9][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH3:8])[N:12]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 74091-PhenylethanolHCID 785042,6-Dichloropyrazine

Product 1

HCID 18186821HCID 18186821, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

K-t-BuO (2.1 g, 18.7 mmol) was added to a stirred solution of 1-phenyl-1-ethanol (2.45 g, 20.1 mmol) in dioxane (30 mL) at 0° C. (ice-bath). After 10 min of stirring, 2,6-dichloropyrazine (2.49 g, 16.7 mmol) was added whereupon the reaction mixture turned orange colored. After being stirrred for a further 1.5 h, ether was added and the mixture was filtered. Concentration in vacuo furnished an orange colored oil that was purified by silica gel chromatography (15×5 cm) using n-hexane ethyl acetate (9:1) as eluent. This gave 3.29 g (84%) of the title compound as a colorless oil. HRMS m/z calcd for C12H11ClN2O (M)+ 234.0560, found 234.0551.

Workup

  1. waitAfter being stirrred for a further 1.5 h
  2. filtrationthe mixture was filtered
  3. concentrationConcentration in vacuo
  4. customfurnished an orange colored oil that
  5. customwas purified by silica gel chromatography (15×5 cm)

Sources & evidence

ORD record
ord-a369ab48d1924a998f6f0827249788a7
Source dataset
uspto-grants-2007_07
Patent number
US07247633B2

Reaction notes

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