Water → HCID 68586628, compound

HRID 2389300Notes

Reaction equation

HRID 2389300 reaction equation
[CH2:1]([Li])CCC.[CH2:6]([O:8][C:9]1[CH:10]([CH3:21])[N:11]=[C:12]([O:18][CH2:19][CH3:20])[C@H:13]([CH:15]([CH3:17])[CH3:16])[N:14]=1)[CH3:7].[Cl:22][C:23]1[CH:28]=[C:27]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=2)[CH:26]=[CH:25][C:24]=1[CH2:40][CH2:41]CI.O>CCCCCC.C1COCC1>[Cl:22][C:23]1[CH:28]=[C:27]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:37])([F:38])[F:39])[CH:31]=2)[CH:26]=[CH:25][C:24]=1[CH:40]([CH3:41])[CH2:21][C@:10]1([CH3:1])[C:9]([O:8][CH2:6][CH3:7])=[N:14][C@@H:13]([CH:15]([CH3:16])[CH3:17])[C:12]([O:18][CH2:19][CH3:20])=[N:11]1

Participants

7

Reactant 4

HCID 962WaterHCID 57935253HCID 57935253, compoundHCID 68586513HCID 68586513, compoundHCID 178418339Butyllithium

Product 1

HCID 68586628HCID 68586628, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Under an argon atmosphere, a solution of n-butyllithium in hexane (1.54 mol/L, 3.59 mL) was added at −78° C. into a solution of (5S)-3,6-diethoxy-5-isopropyl-2-methyl-2,5-dihydropyrazine (905 mg) in THF (16 mL), and the resultant solution was stirred at −78° C. for 30 minutes. Next, A solution of 2-chloro-1-(3-iodopropyl)-4-(3-trifluoromethylphenoxy)benzene (2.47 g) in THF (4 mL) was added to the reaction mixture, and the resultant solution was stirred at −78° C. for 30 minutes and then at 0° C. for 1 hour. To the reaction solution was added water, extracted with ethyl acetate, washed with water and saturated brine in that order, and then dried over anhydrous sodium sulfate. The solvent was evaporated, and the resultant residue was purified by silica gel column chromatography (hexane:ethyl acetate=60:1) to obtain the target product (1.59 g) as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water and saturated brine in that order
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe resultant residue was purified by silica gel column chromatography (hexane:ethyl acetate=60:1)

Sources & evidence

ORD record
ord-9253f31da994461aa333ede447204053
Source dataset
uspto-grants-2012_09
Patent number
US08273748B2

Reaction notes

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