Benzyl 3-phenylpropanoate → (S)-4-Isopropyl-2-phenethyl-4,5-dihydrooxazole

HRID 1365105Notes

Reaction equation

HRID 1365105 reaction equation
[C:1]1([CH2:7][CH2:8][C:9](OCC2C=CC=CC=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:19][C@H:20]([CH2:24][OH:25])[CH:21]([CH3:23])[CH3:22]>ClC1C=CC=CC=1>[CH:21]([C@H:20]1[CH2:24][O:25][C:9]([CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:19]1)([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 562789Benzyl 3-phenylpropanoateHCID 640993L-Valinol

Product 1

HCID 13435839(S)-4-Isopropyl-2-phenethyl-4,5-dihydrooxazoleYield 74%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

Under an argon atmosphere, a mixture of benzyl 3-phenylpropionate (1.5 mmol), (L)-valinol (1.8 mmol), Zn4(OCOCF3)6O (0.15 mmol) and chlorobenzene (2.5 mL) was heated under reflux for 18 hours. From the resulting solution, the solvent was removed using an evaporator, and the residues were purified by silica gel column chromatography to give (S)-4-isopropyl-2-(2-phenylethyl)-1,3-oxazoline in 74% yield. The compound was identified by comparison with physical property data of the known compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 18 hours
  3. customFrom the resulting solution, the solvent was removed
  4. customan evaporator
  5. customthe residues were purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e60c0a1d60a14f5c8d97fe9ed1b937b8
Source dataset
uspto-grants-2011_02
Patent number
US07888513B2

Reaction notes

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