Cesium carbonate → Methyl [3-(5-methyl[1,2,4]oxadiazol-3-yl)phenoxy]-2-phenylacetate

HRID 917575Notes

Reaction equation

HRID 917575 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:9]([O:11][CH3:12])=[O:10].[CH3:19][C:20]1[O:24][N:23]=[C:22]([C:25]2[CH:26]=[C:27]([OH:31])[CH:28]=[CH:29][CH:30]=2)[N:21]=1>C(#N)C>[CH3:19][C:20]1[O:24][N:23]=[C:22]([C:25]2[CH:26]=[C:27]([CH:28]=[CH:29][CH:30]=2)[O:31][CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([O:11][CH3:12])=[O:10])[N:21]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 120425193-(5-Methyl-1,2,4-oxadiazol-3-yl)phenol

Product 1

HCID 12042529Methyl [3-(5-methyl[1,2,4]oxadiazol-3-yl)phenoxy]-2-phenylacetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

11.5 g (33.5 mmol) of caesium carbonate and 7.67 g (35.2 mmol) of methyl 2-bromo-2-phenylacetate are added to a solution of 5.90 g (33.5 mmol) of 3-(5-methyl-1,2,4-oxadiazol-3-yl)phenol in 50 ml of acetonitrile. The reaction mixture is stirred at room temperature for 24 hours, then filtered, and the filtrate is evaporated, giving methyl [3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]-2-phenylacetate as a yellowish oil; ESI 325.

Workup

  1. filtrationfiltered
  2. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-c26fc957916c4454bbe7f96738798dcb
Source dataset
uspto-grants-2007_09
Patent number
US07273867B2

Reaction notes

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