Acetic Acid → HCID 18953973, compound

HRID 1491667Notes

Reaction equation

HRID 1491667 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])[O:11][CH:12]=2)=[CH:4][CH:3]=1.[C:18]1([C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N+]=[N-])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O)(=O)C>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([CH2:13][CH2:14][C:15]([O:17][CH:24]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:16])[O:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 18953969HCID 18953969, compound

Product 1

HCID 18953973HCID 18953973, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(4-chlorophenyl)-2-oxazolepropionic acid (0.5 g) in dichloromethane (20 ml) was added diphenyldiazomethane (0.425 g). After stirring for 4 hours at room temperature, acetic acid (0.5 ml) was added to the mixture. The reaction mixture was washed with a saturated sodium hydrogen carbonate aqueous solution and water, and then dried over MgSO4. The solvent was distilled off and then the oily residue was subjected to a silica gel column chromatography. Crystals of diphenylmethyl 4-(4-chlorophenyl)-2-oxazolepropionate (0.759 g, 91%) were obtained from the fraction eluted with ether-hexane (1:3, V/V). Recrystallization from ether-hexane gave colorless prism crystals of mp 94°-95° C.

Workup

  1. washThe reaction mixture was washed with a saturated sodium hydrogen carbonate aqueous solution and water
  2. dry with materialdried over MgSO4
  3. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-7d5963c6c7be448ab746dc6ecbd59046
Source dataset
uspto-grants-1994_12
Patent number
US05371098

Reaction notes

Loading…