Pyridine → alpha-Cyano-m-phenoxybenzyl alpha-isopropyl-4-trifluoromethoxyphenylacetate

HRID 2050087Notes

Reaction equation

HRID 2050087 reaction equation
[CH:1]([CH:4]([C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1)[C:5](Cl)=[O:6])([CH3:3])[CH3:2].[C:19]([CH:21]([OH:35])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:23]=1)#[N:20].N1C=CC=CC=1>CCOCC>[CH:1]([CH:4]([C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1)[C:5]([O:35][CH:21]([C:19]#[N:20])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:23]=1)=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 93218Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)-HCID 20343288HCID 20343288, compound

Product 1

HCID 54215174alpha-Cyano-m-phenoxybenzyl alpha-isopropyl-4-trifluoromethoxyphenylacetateYield 39.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of α-isopropyl-4-trifluoromethoxyphenylacetyl chloride (4.58 mmol) in ether (5 ml) is added to an ether (20 ml) solution of α-cyano-m-phenoxybenzyl alcohol (4.58 mmol) and pyridine (0.5 ml). The mixture is stirred overnight and filtered. The filtrate and the washings are evaporated and the residual oil is purified on 5×2 mm silica gel plates using 1:1 methylenechloride-hexane as eluent. The band with Rf=0.55 is extracted with ether and evaporated to give the desired ester (0.85 g).

Workup

  1. filtrationfiltered
  2. customThe filtrate and the washings are evaporated
  3. customthe residual oil is purified on 5×2 mm silica gel plates
  4. extractionThe band with Rf=0.55 is extracted with ether
  5. customevaporated

Sources & evidence

ORD record
ord-beac2b840ec04b7595d15a1d9eee9e1a
Source dataset
uspto-grants-1980_04
Patent number
US04199595

Reaction notes

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