Toluene → HCID 89499006, compound

HRID 588667Notes

Reaction equation

HRID 588667 reaction equation
[CH3:1][C:2]12[CH2:12][CH:6]3[CH2:7][C:8]([CH3:11])([CH2:10][C:4]([CH2:13][N:14]4[CH:18]=[CH:17][CH:16]=[N:15]4)([CH2:5]3)[CH2:3]1)[CH2:9]2.[C:19]1(C)C=CC=CC=1.C([Li])CCC.CI>O1CCCC1>[CH3:11][C:8]12[CH2:7][CH:6]3[CH2:12][C:2]([CH3:1])([CH2:3][C:4]([CH2:13][N:14]4[C:18]([CH3:19])=[CH:17][CH:16]=[N:15]4)([CH2:5]3)[CH2:10]1)[CH2:9]2

Participants

6

Reactant 4

HCID 1140TolueneHCID 6328Methyl iodideHCID 89499008HCID 89499008, compoundHCID 178418339Butyllithium

Product 1

HCID 89499006HCID 89499006, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 32A (2.44 g) in tetrahydrofuran (25 mL)/toluene (25 mL) was added n-butyllithium (7.49 mL) at −40° C. The reaction mixture was stirred for 60 minutes when CH3I (1.873 mL) was added and the stirring was continued for 2 hours at −40° C. The reaction mixture was quenched with saturated ammonium chloride solution, extracted with ethyl acetate, dried over magnesium sulfate, filtered, concentrated and purified by flash chromotography (silica gel, 0%-15% ethyl acetate/hexanes).

Workup

  1. additionwas added
  2. customThe reaction mixture was quenched with saturated ammonium chloride solution
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromotography (silica gel, 0%-15% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2f6c5ddd7fbb4f529e62eaa7e51521dd
Source dataset
uspto-grants-2016_01
Patent number
US09227963B2

Reaction notes

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