Acetone → 1-(6-Bromoquinoline-2-yl)-2-methylpropane-2-ol

HRID 601691

Reaction equation

HRID 601691 reaction equation
C(OCC)C.[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([CH3:17])[CH:11]=[CH:10]2.C([Li])CCC.[CH3:23][C:24]([CH3:26])=[O:25]>O>[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([CH2:17][C:24]([CH3:26])([OH:25])[CH3:23])[CH:11]=[CH:10]2

Participants

6

Reactant 4

HCID 180AcetoneHCID 3283Diethyl EtherHCID 5228856-Bromo-2-methylquinolineHCID 178418339Butyllithium

Product 1

HCID 231582271-(6-Bromoquinoline-2-yl)-2-methylpropane-2-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

20 ml of diethylether was added to 2.22 g of 6-bromoquinaldine, and 3.76 ml of 2.66 M normal butyl lithium was dropped thereto at −78° C. The obtained suspension was stirred for 5 min, 2 ml of anhydrous acetone was added and the mixture was further stirred for 10 min, and water was added. The products were extracted with ethyl acetate, organic layer was dried with anhydrous sodium sulfated and the solvents were distilled outunder reduced pressure. The obtained residues were separated and purified by silicagel colum chromatography (hexane:ethyl acetate=2:1) to obtain 1.14 g of the above compound.

Workup

  1. additionwas dropped
  2. customat −78° C
  3. stirringthe mixture was further stirred for 10 min
  4. extractionThe products were extracted with ethyl acetate, organic layer
  5. dry with materialwas dried with anhydrous sodium
  6. distillationthe solvents were distilled outunder reduced pressure
  7. customThe obtained residues were separated
  8. custompurified by silicagel colum chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-a056bae2b55a41a387e3634c7b8d9f63
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Linked notes

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