Potassium tert-butoxide → HCID 66991689, compound

HRID 557419Notes

Reaction equation

HRID 557419 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:22](=O)[CH3:23])[C:15]([O:17][CH:18]1[CH2:21][CH2:20][CH2:19]1)=[O:16].[NH2:25][C:26]([C:30]([F:33])([F:32])[F:31])=[CH:27][C:28]#[N:29].CC(C)([O-])C.[K+]>CC(O)C>[C:28]([C:27]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][CH:18]2[CH2:19][CH2:20][CH2:21]2)=[O:16])=[C:22]([CH3:23])[NH:25][C:26]=1[C:30]([F:33])([F:32])[F:31])#[N:29]

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 534010963-Amino-4,4,4-trifluorobut-2-enenitrileHCID 66991397HCID 66991397, compound

Product 1

HCID 66991689HCID 66991689, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 345 mg (1.06 mmol) of cyclobutyl 2-[(2-methyl-4-oxo-4H-chromen-8-yl)methylene]-3-oxobutanoate in 30 ml of 2-propanol is mixed with 143.85 mg (1.06 mmol) of 3-amino-4,4,4-trifluorobut-2-enenitrile [preparation in analogy to K. Krespan, J. Org. Chem. 34, 42-45 (1969)] and 17.8 mg (0.16 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-1fe1b42621a84426aa513a0a74400b77
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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