Benzenepropanoic acid → (S)-4-Isopropyl-2-phenethyl-4,5-dihydrooxazole

HRID 1365101Notes

Reaction equation

HRID 1365101 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:12][C@H:13]([CH2:17]O)[CH:14]([CH3:16])[CH3:15]>ClC1C=CC=CC=1>[CH:14]([C@H:13]1[CH2:17][O:11][C:9]([CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:12]1)([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 107Benzenepropanoic acidHCID 640993L-Valinol

Product 1

HCID 13435839(S)-4-Isopropyl-2-phenethyl-4,5-dihydrooxazoleYield 86%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

Under an argon atmosphere, a mixture of 3-phenylpropionic acid (3.0 mmol), (L)-valinol (3.6 mmol), Zn4(OCOCF3)6O (0.15 mmol) and chlorobenzene (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-(2-phenylethyl)-1,3-oxazoline in 86% 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-a7970cc0ba3f48908a2f943eb9c439c1
Source dataset
uspto-grants-2011_02
Patent number
US07888513B2

Reaction notes

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