Potassium tert-butoxide → HCID 66991811, compound

HRID 557421Notes

Reaction equation

HRID 557421 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=[C:14]([C:20](=O)[CH3:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16].[NH2:23][C:24]([C:28]([F:31])([F:30])[F:29])=[CH:25][C:26]#[N:27].CC(C)([O-])C.[K+]>CC(O)C>[C:26]([C:25]1[CH:13]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[O:3][C:2]([CH3:1])=[CH:11][C:10]3=[O:12])[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:20]([CH3:21])[NH:23][C:24]=1[C:28]([F:31])([F:30])[F:29])#[N:27]

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 534010963-Amino-4,4,4-trifluorobut-2-enenitrileHCID 66991894HCID 66991894, compound

Product 1

HCID 66991811HCID 66991811, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 310 mg (1.03 mmol) of ethyl 2-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]-3-oxobutanoate in 30 ml of 2-propanol is mixed with 140.47 mg (1.03 mmol) of 3-amino-4,4,4-trifluorobut-2-enenitrile [preparation analogous to K. Krespan, J. Org. Chem. 34, 42-45 (1969)] and 17.38 mg (0.15 mmol) of potassium tert-butoxide and stirred under reflux for 12 h. After cooling, the mixture is concentrated. The residue is purified on an Analogix cartridge (F12M) (mobile phase: cyclohexane/ethyl acetate 2:1). After concentration of the product fractions, the residue is crystallized from diethyl ether. 50.9 mg (10.8% of theory) of the title compound are obtained as white crystals.

Workup

  1. temperatureunder reflux for 12 h
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated
  4. customThe residue is purified on an Analogix cartridge (F12M) (mobile phase: cyclohexane/ethyl acetate 2:1)
  5. customAfter concentration of the product fractions, the residue is crystallized from diethyl ether

Sources & evidence

ORD record
ord-f952a11c2db649929a58208b96351a0f
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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