Water → HCID 67287853, compound

HRID 879957Notes

Reaction equation

HRID 879957 reaction equation
[CH2:1]([CH:4]1[C:9]([O:10][CH3:11])=[N:8][C@H:7]([CH:12]([CH3:14])[CH3:13])[C:6]([O:15][CH3:16])=[N:5]1)[CH:2]=[CH2:3].[Br:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25]I)=[C:20]([Cl:27])[CH:19]=1.O>O1CCCC1>[CH2:1]([C@:4]1([CH2:25][CH2:24][C:21]2[CH:22]=[CH:23][C:18]([Br:17])=[CH:19][C:20]=2[Cl:27])[C:9]([O:10][CH3:11])=[N:8][C@H:7]([CH:12]([CH3:14])[CH3:13])[C:6]([O:15][CH3:16])=[N:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 962WaterHCID 462025614-Bromo-2-chloro-1-(2-iodoethyl)benzeneHCID 67286971HCID 67286971, compound

Product 1

HCID 67287853HCID 67287853, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Under an argon atmosphere, an n-butyllithium-hexane solution (1.60 mol/L, 11.16 mL) was added at −78° C. to a solution of (5R)-2-allyl-3,6-dimethoxy-5-isopropyl-2,5-dihydropyrazine (3.64 g) in tetrahydrofuran (60 mL) to form a reaction solution. This reaction solution was then stirred at −78° C. for 30 minutes. A solution of 4-bromo-2-chloro-1-(2-iodoethyl)benzene (6.73 g) in tetrahydrofuran (20 mL) was added to the reaction solution, and the reaction solution was stirred at −78° C. for 30 minutes and then at 0° C. for 1 hour. Water was added to the reaction solution, and the reaction solution was extracted with ethyl acetate. The extract was washed with water and saturated brine in that order, and then dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was removed by filtration, and then the solvent was removed by distillation under reduced pressure. The resultant product was purified by silica gel column chromatography (hexane:ethyl acetate=70:1) to obtain the target product (6.04 g) as a colorless oil.

Workup

  1. customto form a reaction solution
  2. stirringthe reaction solution was stirred at −78° C. for 30 minutes
  3. waitat 0° C. for 1 hour
  4. extractionthe reaction solution was extracted with ethyl acetate
  5. washThe extract was washed with water and saturated brine in that order
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe anhydrous sodium sulfate was removed by filtration
  8. customthe solvent was removed by distillation under reduced pressure
  9. customThe resultant product was purified by silica gel column chromatography (hexane:ethyl acetate=70:1)

Sources & evidence

ORD record
ord-211d0093470a4e8b9a7911e22cde7c52
Source dataset
uspto-grants-2015_03
Patent number
US08993543B2

Reaction notes

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