Triethylamine → HCID 178499206, compound

HRID 1861602Notes

Reaction equation

HRID 1861602 reaction equation
[CH3:1][C:2]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[OH:15][C:16]1[C:17]([O:28][CH3:29])([C:24]([O:26][CH3:27])=[O:25])[CH2:18][CH:19]([CH3:23])[C:20](=[O:22])[CH:21]=1.C(N(CC)CC)C.[C-]#N.[K+]>C(#N)C>[OH:15][C:16]1[C:17]([O:28][CH3:29])([C:24]([O:26][CH3:27])=[O:25])[CH2:18][CH:19]([CH3:23])[C:20](=[O:22])[C:21]=1[C:4]([C:3]1[C:2]([CH3:1])=[N:10][C:9]([C:11]([F:14])([F:13])[F:12])=[CH:8][CH:7]=1)=[O:5]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9032Potassium CyanideHCID 27756752-Methyl-6-(trifluoromethyl)nicotinoyl chlorideHCID 18755506Methyl 2-hydroxy-1-methoxy-5-methyl-4-oxocyclohex-2-enecarboxylate

Product 1

HCID 178499206HCID 178499206, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.23 g of fresh 2-methyl-6-trifluoromethylnicotinoyl chloride are added to a mixture of 2.14 g of methyl 2-hydroxy-1-methoxy-5-methyl-4-oxocyclohex-2-enecarboxylate and 2.02 g of triethylamine in 30 ml of acetonitrile. After approximately 30 minutes, 0.065 g of potassium cyanide is added and the mixture is stirred for 18 hours. At pH 2, the mixture is subsequently partitioned between water and ethyl acetate, dried over magnesium sulfate and evaporated. Filtration on silica gel (mobile phase ethyl acetate/methanoltriethylamine 85:10:5) gives the pure methyl 2-hydroxy-1-methoxy-methyl-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)-4-oxocyclohex-2-enecarboxylate as a viscous oil.

Workup

  1. customAt pH 2, the mixture is subsequently partitioned between water and ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. filtrationFiltration on silica gel (mobile phase ethyl acetate/methanoltriethylamine 85:10:5)

Sources & evidence

ORD record
ord-a1be791e6a924c74b01f5b2d669397ff
Source dataset
uspto-grants-2003_03
Patent number
US06534445B1

Reaction notes

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