Water → HCID 68586628, compound

HRID 445427Notes

Reaction equation

HRID 445427 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-a3ac4306d9a94ee8825f4865aac87f33
Source dataset
uspto-grants-2013_07
Patent number
US08476305B2

Reaction notes

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