p-METHYLACETOPHENONE → HCID 23017953, compound

HRID 1788370Notes

Reaction equation

HRID 1788370 reaction equation
[CH3:1][S:2]([C:5]1[CH:23]=[CH:22][C:8]([O:9][CH2:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[C:13]([CH3:21])[CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C([N-]C(C)C)(C)C.[Li+].[CH3:32][C:33]1[CH:38]=[CH:37][C:36]([C:39](=[O:41])[CH3:40])=[CH:35][CH:34]=1>O1CCCC1.[Cl-].[Na+].O>[CH3:21][C:13]1[CH:12]=[C:11]([CH2:10][O:9][C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH2:1][C:39]([C:36]3[CH:37]=[CH:38][C:33]([CH3:32])=[CH:34][CH:35]=3)([OH:41])[CH3:40])(=[O:4])=[O:3])=[CH:23][CH:22]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1

Participants

6

Reactant 3

HCID 8500p-METHYLACETOPHENONEHCID 2724682Lithium diisopropylamideHCID 230180214-(4-Methanesulfonylphenoxymethyl)-2-methylquinoline

Product 1

HCID 23017953HCID 23017953, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

Under an atmosphere of argon, a solution of 473 mg (1.44 mmol) of 4-(4-methanesulfonylphenoxymethyl)-2-methylquinoline in tetrahydrofuran was cooled to −78° C. and then, 1.44 mL (1.44 mmol) of 2 M lithium diisopropylamide was added thereto and stirred for 40 minutes. Into this solution was dropped a solution of 194 mg (1.59 mmol) of p-methylacetophenone in tetrahydrofuran, followed by stirring for 2.5 hours. The reaction was stopped by the addition of saturated brine, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and filtered, and the filtrate was concentrated under a reduced pressure. The obtained residue was purified by column chromatography on silica gel (developing solvent; hexane:ethyl acetate=1:1 to 1:2) to obtain 440 mg (0.95 mmol) of 1-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonyl]-2-p-tolylpropan-2-ol (VIII-57). Its physical property is shown below.

Workup

  1. stirringby stirring for 2.5 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under a reduced pressure
  6. customThe obtained residue was purified by column chromatography on silica gel (developing solvent; hexane:ethyl acetate=1:1 to 1:2)

Sources & evidence

ORD record
ord-97adc6632ffe4899b931aa4034848e5d
Source dataset
uspto-grants-2009_03
Patent number
US07511144B2

Reaction notes

Loading…