1-(Bromomethyl)-3-ethylbenzene → 2-[2-[2-(3-Ethylphenyl)ethyl]-4-methylphenyl]-4,5-dihydro-4,4-dimethyloxazole

HRID 1871983

Reaction equation

HRID 1871983 reaction equation
C([Li])CCC.[CH3:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[C:14]1[O:15][CH2:16][C:17]([CH3:20])([CH3:19])[N:18]=1.Br[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][CH3:30])[CH:24]=1>CCCC(C)C.O1CCCC1>[CH2:29]([C:25]1[CH:24]=[C:23]([CH2:22][CH2:6][C:7]2[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=2[C:14]2[O:15][CH2:16][C:17]([CH3:20])([CH3:19])[N:18]=2)[CH:28]=[CH:27][CH:26]=1)[CH3:30]

Participants

6

Reactant 3

HCID 220036561-(Bromomethyl)-3-ethylbenzeneHCID 221172732-[2,4-Dimethylphenyl]-4,5-dihydro-4,4-dimethyloxazoleHCID 178418339Butyllithium

Product 1

HCID 186897132-[2-[2-(3-Ethylphenyl)ethyl]-4-methylphenyl]-4,5-dihydro-4,4-dimethyloxazole

Reagents, catalysts & solvents 2

HCID 78922-MethylpentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

n-Butyllithium (16.8 ml of a 2.5M solution in isohexane) was added dropwise to a stirred solution of the product of step (iii) (8.13 g) in dry tetrahydrofuran (ISOml) at 0° C. under nitrogen. After 1 hour, the product of step (ii) (8.0 g) in tetrahydrofliran (60 ml) was added. After 1 hour, the reaction was quenched with aqueous ammonium chloride and partitioned between ethyl acetate and water. The organic solution was dried (MgSO4) and evaporated. Purification was by chromatography eluting with 5% ethyl acetate in isohexane. Yield 4.93 g.

Workup

  1. waitAfter 1 hour
  2. customthe reaction was quenched with aqueous ammonium chloride
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe organic solution was dried (MgSO4)
  5. customevaporated
  6. customPurification
  7. washeluting with 5% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-6131338cbdc04d71916f960b0699ee4f
Source dataset
uspto-grants-2000_08
Patent number
US06107297

Linked notes

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