Methyl Benzoate → (S)-4-isopropyl-2-phenyloxazoline

HRID 1039804Notes

Reaction equation

HRID 1039804 reaction equation
[C:1]([O:9][CH3:10])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:11][C@H:12](CO)[CH:13]([CH3:15])[CH3:14]>[Zn].ClC1C=CC=CC=1>[CH:13]([C@H:12]1[CH2:10][O:9][C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:11]1)([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 7150Methyl BenzoateHCID 640993L-Valinol

Product 1

HCID 10947327(S)-4-isopropyl-2-phenyloxazolineYield 84%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 7964ChlorobenzeneSolvent

Procedure

Under a nitrogen atmosphere, a mixture of methyl benzoate (1.5 mmol), (S)-valinol (1.8 mmol), a zinc cluster Zn4O (OCOCF3)6 (0.0375 mmol), and chlorobenzene (2.5 ml) was refluxed for 12 hours. As a result, (S)-4-isopropyl-2-phenyloxazoline was obtained in a yield of 84%.

Sources & evidence

ORD record
ord-815567aaca864708a3729b756d493b17
Source dataset
uspto-grants-2013_10
Patent number
US08552204B2

Reaction notes

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