Acetone → 2-[3,5-Di(2-methylallyl)phenyl]oxazolo[4,5-b]pyridine

HRID 66387

Reaction equation

HRID 66387 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([C:11]2[O:12][C:13]3[C:14]([N:19]=2)=[N:15][CH:16]=[CH:17][CH:18]=3)[CH:6]=[C:7]([CH2:9]Br)[CH:8]=1.[C:20]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:25]=CC=C[CH:21]=1.[PH4+].[O-]CC.[Li+].[CH3:44][C:45]([CH3:47])=O>O.C(O)C.CN(C)C=O>[CH3:25][C:20](=[CH2:21])[CH2:2][C:3]1[CH:4]=[C:5]([C:11]2[O:12][C:13]3[C:14]([N:19]=2)=[N:15][CH:16]=[CH:17][CH:18]=3)[CH:6]=[C:7]([CH2:9][C:45]([CH3:47])=[CH2:44])[CH:8]=1

Participants

9

Reactant 5

HCID 180AcetoneHCID 11776TriphenylphosphineHCID 5460504PhosphoniumHCID 227548282-[3,5-Bis(bromomethyl)phenyl][1,3]oxazolo[4,5-b]pyridineHCID 23661847Lithium ethoxide

Product 1

HCID 227547782-[3,5-Di(2-methylallyl)phenyl]oxazolo[4,5-b]pyridine

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5 mmoles of the product from Step A and 11.0 mmoles of triphenylphosphine in 15 ml. of dimethylformamide is stirred and refluxed under nitrogen for 3 hours. The mixture is cooled and the phosphonium salt is collected on a filter. A mixture of 4 mmoles of the phosphonium salt, 100 ml. of ethanol, 1 ml. of acetone and 40 ml. of 0.3 N ethanolic lithium ethoxide is stirred at room temperature under nitrogen for 2 hours. Water (100 ml.) is added and the mixture is cooled in an ice-bath. The precipitate is collected and purified by chromatography on silica gel using 2% methanol in chloroform as the eluant to give 2-[3,5-di(2-methylallyl)phenyl]oxazolo[4,5-b]pyridine.

Workup

  1. temperaturerefluxed under nitrogen for 3 hours
  2. temperatureThe mixture is cooled
  3. customthe phosphonium salt is collected on a filter
  4. temperaturethe mixture is cooled in an ice-bath
  5. customThe precipitate is collected
  6. custompurified by chromatography on silica gel using 2% methanol in chloroform as the eluant

Sources & evidence

ORD record
ord-d3b0b6db65ed4ff39866941040eacc9e
Source dataset
uspto-grants-1978_12
Patent number
US04131677

Linked notes

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