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Carbon Dioxide → 3-Ethyl 5-hydrogen 2,6-bis(trifluoromethyl)-4-ethoxy-3,5-pyridinedicarboxylate

HRID 1763115
Notes
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Reaction equation

HRID 1763115 reaction equation
[Li+].CC([N-]C(C)C)C.[F:9][C:10]([F:30])([F:29])[C:11]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([O:22][CH2:23][CH3:24])[CH:14]=[C:13]([C:25]([F:28])([F:27])[F:26])[N:12]=1.[C:31](=[O:33])=[O:32]>COCCOC>[F:30][C:10]([F:29])([F:9])[C:11]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([O:22][CH2:23][CH3:24])[C:14]([C:31]([OH:33])=[O:32])=[C:13]([C:25]([F:28])([F:27])[F:26])[N:12]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 2724682Lithium diisopropylamide2×HCID 13882869Ethyl 2,6-bis(trifluoromethyl)-4-ethoxy-3-pyridinecarboxylate2×

Product 1

HCID 140137533-Ethyl 5-hydrogen 2,6-bis(trifluoromethyl)-4-ethoxy-3,5-pyridinedicarboxylateYield 52.7%

Reagents, catalysts & solvents 1

HCID 8071
1,2-Dimethoxyethane
Solvent

Conditions

Temperature
-78 °C

Procedure

This material was prepared in 52.7% yield from 0.06 mol of LDA and 0.024 mol of product of Example 6 according to the following general procedure as a beige solid, mp 115°-117° C. To a -78° C. solution of 2.5 eq (0.06 mol) of LDA in DMEwas added a solution of 1 eq (0.024 mol) of starting material, the monocarboxylate product (Example 6) in dry DME. The resulting dark colored solution was stirred for 30 minutes at -78° C. To the above solution was added excess of dry ice. The reaction mixture was stirred at -78° C. for 15 minutes and warmed to room temperature in 1 hour. The reaction mixture was poured into ice water (100 ml) and extracted with ether. The aqueous layer was made acidic. The oil precipitate was extracted with ether. The ether extract was dried (MgSO4) and concentrated in vacuo to give the desired product.

Workup

  1. stirringThe reaction mixture was stirred at -78° C. for 15 minutes
  2. temperaturewarmed to room temperature in 1 hour
  3. extractionextracted with ether
  4. extractionThe oil precipitate was extracted with ether
  5. extractionThe ether extract
  6. dry with materialwas dried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-14a705e7a7d84640a0679be24484e873
Source dataset
uspto-grants-1989_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04835279

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes