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Allyl bromide → Ethyl 2,6-bis(trifluoromethyl)-4-allyloxy-3-pyridinecarboxylate

HRID 542105
Notes
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Reaction equation

HRID 542105 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([OH:14])[CH:6]=[C:5]([C:15]([F:18])([F:17])[F:16])[N:4]=1.C([O-])([O-])=O.[K+].[K+].[CH2:27](Br)[CH:28]=[CH2:29]>CC(C)=O>[F:20][C:2]([F:19])([F:1])[C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([O:14][CH2:29][CH:28]=[CH2:27])[CH:6]=[C:5]([C:15]([F:18])([F:17])[F:16])[N:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 178470034HCID 178470034, compound

Product 1

HCID 13882865Ethyl 2,6-bis(trifluoromethyl)-4-allyloxy-3-pyridinecarboxylateYield 90.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6.06 g (0.02 mol) of product of Example 3, 2.8 g (0.02 mol) of K2CO3, 30 g of allyl bromide, and 50 ml of acetone was held at reflux for 4 hours and concentrated. The residue was treated with water and extracted into ether. The ether solution was dried and concentrated. The residue was kugelrohr distilled at 133 Pa (pot temperature 110° C.) to give 6.2 g (90%) of product, nD25 1.4330.

Workup

  1. temperatureat reflux for 4 hours
  2. concentrationconcentrated
  3. additionThe residue was treated with water
  4. extractionextracted into ether
  5. dry with materialThe ether solution was dried
  6. concentrationconcentrated
  7. distillationThe residue was kugelrohr distilled at 133 Pa (pot temperature 110° C.)

Sources & evidence

ORD record
ord-26c023d122bb42b1b20082f66afef5e5
Source dataset
uspto-grants-1987_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04655816

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes