2-[2,4-Dimethylphenyl]-4,5-dihydro-4,4-dimethyloxazole → 4,5-Dihydro-4,4-dimethyl-2-[4-methyl-2-[2-[2,3-dimethylphenyl]ethyl]phenyl]oxazole

HRID 1275905

Reaction equation

HRID 1275905 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6][C:7]1([CH3:20])[CH2:11][O:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=2[CH3:19])=[N:8]1>O1CCCC1>[CH3:6][C:7]1([CH3:20])[CH2:11][O:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=2[CH2:19][CH2:1][C:2]2[CH:14]=[CH:13][CH:12]=[C:17]([CH3:16])[C:3]=2[CH3:4])=[N:8]1

Participants

4

Reactant 2

HCID 221172732-[2,4-Dimethylphenyl]-4,5-dihydro-4,4-dimethyloxazoleHCID 178418339Butyllithium

Product 1

HCID 221172044,5-Dihydro-4,4-dimethyl-2-[4-methyl-2-[2-[2,3-dimethylphenyl]ethyl]phenyl]oxazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyllithium (6.9 ml of a 2.5M soln in hexanes) was added dropwise to the product of example 21 step (i) (3.51 g) in tetrahydrofuran (60 ml) at -78° C. After 2 hours the product from step (i) (3.45 g) was added. After 1 hour the solution was left to warm to room temperature. The solution was quenched with water and extracted with ethyl acetate. The organic solution was dried (MgSO4) and evaporated under reduced pressure. Yield 1.83 g.

Workup

  1. customThe solution was quenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic solution was dried (MgSO4)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-91762cdd6cfb4b918869ccc2090b8faa
Source dataset
uspto-grants-2000_12
Patent number
US06162808

Linked notes

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