Triethylamine → 2-(4-Ethylphenyl)-4,4-dimethyl-2-oxazoline

HRID 990787Notes

Reaction equation

HRID 990787 reaction equation
[CH2:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH2:31][C:32]([CH3:36])([CH3:35])[CH2:33]O.C(N(CC)CC)C>C(#N)C.CCCCCC.C(OCC)(=O)C.ClC(Cl)(Cl)Cl>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C:7]2[O:9][CH2:33][C:32]([CH3:36])([CH3:35])[N:31]=2)=[CH:10][CH:11]=1)[CH3:2]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 118072-Amino-2-methyl-1-propanolHCID 120864-Ethylbenzoic Acid

Product 1

HCID 128725592-(4-Ethylphenyl)-4,4-dimethyl-2-oxazoline

Reagents, catalysts & solvents 4

HCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-ethylbenzoic acid (3.80 g) in anhydrous acetonitrile (100 mL) was added under a nitrogen atmosphere, triphenylphosphine (20 g), 2-amino-2-methyl-1-propanol (2.74 mL) and triethylamine (28.2 mL). The mixture was cooled on an ice bath and then tetrachloromethane (5.36 mL) was added. The reaction mixture was allowed to stand at room temperature and stirred for 18 hours. To the reaction mixture was added ethyl acetate and hexane and the precipitate was removed by filtration. The concentration of the filtrate left a residue, which was purified by column chromatography on silica gel (hexane/ethyl acetate/=9/1/to 6/1) to give the subject compound (1.15 g).

Workup

  1. temperatureThe mixture was cooled on an ice bath
  2. customto stand at room temperature
  3. customthe precipitate was removed by filtration
  4. waitThe concentration of the filtrate left a residue, which
  5. customwas purified by column chromatography on silica gel (hexane/ethyl acetate/=9/1/to 6/1)

Sources & evidence

ORD record
ord-e244bfcd420c409f8f02c5985eac87e8
Source dataset
uspto-grants-2002_10
Patent number
US06462053B1

Reaction notes

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