Hydrochloric Acid → HCID 58586423, compound

HRID 2116667Notes

Reaction equation

HRID 2116667 reaction equation
[C:1]([O:5][C:6]([CH2:8][CH:9]([C:12]#[N:13])[C:10]#[N:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:14][C:15]([F:21])([F:20])[CH2:16][CH2:17][CH2:18]Br.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[C:1]([O:5][C:6]([CH2:8][C:9]([CH2:18][CH2:17][CH2:16][C:15]([F:21])([F:20])[F:14])([C:12]#[N:13])[C:10]#[N:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 5210064-Bromo-1,1,1-trifluorobutaneHCID 58586409tert-Butyl 3,3-dicyanopropanoate

Product 1

HCID 58586423HCID 58586423, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.48 g of 2-(tert-butoxycarbonylmethyl)malononitrile and 0.32 g of 1,1,1-trifluoro-4-bromobutane were dissolved in 2 ml of N,N-dimethylformamide, and to the solution was added 0.40 g of potassium carbonate followed by stirring for 5 hours at room temperature. Then, to the reaction mixture was added dilute hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was subjected to silica gel column chromatography to give 0.33 g of 2-(tert-butoxycarbonylmethyl)-2-(4,4,4-trifluorobutyl)malononitrile (hereinafter referred to as the present invention compound (51)).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained

Sources & evidence

ORD record
ord-d35b10c84cd14ef4837d69d9c895df03
Source dataset
uspto-grants-2008_10
Patent number
US07439266B2

Reaction notes

Loading…