2,6-Dichloropyrazine → HCID 18186851, compound

HRID 1357596Notes

Reaction equation

HRID 1357596 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([OH:11])[CH2:3][CH2:2]1.[Cl:12][C:13]1[CH:18]=[N:17][CH:16]=[C:15](Cl)[N:14]=1>O1CCOCC1.ClCCl>[Cl:12][C:13]1[CH:18]=[N:17][CH:16]=[C:15]([O:11][CH:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[O:1][CH2:2][CH2:3]2)[N:14]=1

Participants

5

Reactant 2

HCID 785042,6-DichloropyrazineHCID 92890Chroman-4-ol

Product 1

HCID 18186851HCID 18186851, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

K-t-BuO (1.28 g, 11.42 mmol) was added to a stirred solution of 4-chromanol (1.81 g, 12.0 mmol) in dioxane (30 mL) at 0° C. (ice-bath). After being stirred for 5 min at room temperature, the mixture was chilled to 0° C. (ice-bath) and 2,6-dichloropyrazine (1.49 g, 10.0 mmol) was added. The reaction mixture was stirred at room temperature for 15 min and diluted with dichloromethane. Filtration and concentration in vacuo furnished an orange thick oil which was purified by chromatography on silica gel (15×4 cm) using n-hexane/ethyl acetate (8:2) as eluent. This furnished 1.87 g (71%) of the title compound as a colorless oil. HRMS m/z calcd for C13H11ClN2O2 (M)+ 262.0509, found 262.0520. Anal. (C13H11ClN2O2) C, H, N.

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred at room temperature for 15 min
  3. filtrationFiltration and concentration in vacuo
  4. customfurnished an orange thick oil which
  5. customwas purified by chromatography on silica gel (15×4 cm)

Sources & evidence

ORD record
ord-95b20f57a4654808b2a85a24f38d0465
Source dataset
uspto-grants-2003_07
Patent number
US06593330B2

Reaction notes

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