Benzaldehyde → trans-4-Methoxycarbonyl-5-phenyl-2-oxazoline

HRID 653822Notes

Reaction equation

HRID 653822 reaction equation
C(N)C.[N+:4]([CH2:6][C:7]([O:9][CH3:10])=[O:8])#[C-:5].[CH:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCCCCC.C(OCC)(=O)C>ClCCl.N#N>[CH3:10][O:9][C:7]([C@H:6]1[C@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:18][CH:5]=[N:4]1)=[O:8]

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 6341EthylamineHCID 547815Methyl isocyanoacetateHCID 21226206Ethyl acetate hexane

Product 1

HCID 11195076trans-4-Methoxycarbonyl-5-phenyl-2-oxazolineYield 84.6%

Reagents, catalysts & solvents 2

HCID 947NitrogenSolventHCID 6344DichloromethaneSolvent

Procedure

27.5 mg (0.055 mmol) of bis(cyclohexylisocyanide)-gold tetrafluoroborate, 39.7 mg (0.056 mmol) of (R)-N-methyl-N-[2-(diethylamino)-ethyl]-1-[(S)-1',2bis(-ethylamine and 0.549 g (5.54 mmol) of methyl isocyano-acetate were dissolved in 5.5 ml of dry dichloromethane, and 0.642 g (6.05 mmol) of benzaldehyde was added thereto. The reaction mixture was reacted for 20 hours at 25° C in N2 atmosphere. After the solvent was concentrated, the residue formed was subjected to silica-gel column chromatography (solvent: hexane/ethyl acetate =1/2) to obtain 0.96 mg (84.6%) of trans-4-methoxycarbonyl-5- phenyl-2-oxazoline and 0.12 g (10.4%) of the corresponding cis-form.

Workup

  1. concentrationAfter the solvent was concentrated
  2. customthe residue formed

Sources & evidence

ORD record
ord-e732476da88f45138eac23e933cb4f0c
Source dataset
uspto-grants-1992_07
Patent number
US05128478

Reaction notes

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