Potassium Carbonate → Ethyl 4-[4-(2-nitro-4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-pentenoate

HRID 1248527Notes

Reaction equation

HRID 1248527 reaction equation
[N+:1]([C:4]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)([O-:3])=[O:2].Br[CH:23]([CH3:33])[C:24]([O:31][CH3:32])=[CH:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[N+:1]([C:4]1[CH:17]=[C:16]([C:18]([F:19])([F:20])[F:21])[CH:15]=[CH:14][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH:23]([CH3:33])[C:24]([O:31][CH3:32])=[CH:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:9][CH:8]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 233251014-[2-Nitro-4-(trifluoromethyl)phenoxy]phenolHCID 53787831Ethyl 4-bromo-3-methoxypent-2-enoate

Product 1

HCID 53972465Ethyl 4-[4-(2-nitro-4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-pentenoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-(2-nitro-4-trifluoromethylphenoxy) phenol (9.36 mm)., ethyl 4-bromo-3-methoxy-2-pentenoate (12 mm.) and K2CO3 (14 mm.) in acetone (20 ml.) is refluxed for 24 hours. After filtration, the filtrate is concentrated and the oily residue chromatographed on silica gel to yield ethyl 4-[4-(2-nitro-4-trifluoromethylphenoxy) phenoxy]-3-methoxy-2-pentenoate.

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate is concentrated
  3. customthe oily residue chromatographed on silica gel

Sources & evidence

ORD record
ord-191e9d2f192849a995f4b4ae714d27c9
Source dataset
uspto-grants-1985_06
Patent number
US04525205

Reaction notes

Loading…