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

HRID 1365100Notes

Reaction equation

HRID 1365100 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 83%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 7964ChlorobenzeneSolvent

Procedure

Under an argon atmosphere, a mixture of methyl benzoate (1.5 mmol), (L)-valinol (1.8 mmol), Zn4(OCOCF3)6O (0.15 mmol in terms of the number of moles of zinc atom; the number of moles of the zinc compound used in the following Examples is also shown in terms of the number of moles of zinc atom) and chlorobenzene (2.5 mL) was heated under reflux for 12 hours. From the resulting solution, the solvent was removed using an evaporator, and the residues were purified by silica gel column chromatography (hexane/ethyl acetate=10/1 (V/V)) to give (S)-4-isopropyl-2-phenyl-1,3-oxazoline in 83% yield.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 12 hours
  3. customFrom the resulting solution, the solvent was removed
  4. customan evaporator
  5. customthe residues were purified by silica gel column chromatography (hexane/ethyl acetate=10/1 (V/V))

Sources & evidence

ORD record
ord-9288b1d0572c420ab1726fcf1d256333
Source dataset
uspto-grants-2011_02
Patent number
US07888513B2

Reaction notes

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