Diisopropylamine → ethyl 3-(diisopropylamino)-4,4-difluorobut-3-enoate

HRID 732269Notes

Reaction equation

HRID 732269 reaction equation
[CH:1]([NH:4][CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].COP(O[C:15](=[C:22]([F:24])[F:23])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])(OC)=O>COC(C)(C)C>[CH:1]([N:4]([CH:5]([CH3:7])[CH3:6])[C:15](=[C:22]([F:24])[F:23])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 7912DiisopropylamineHCID 11492794ethyl 3-[(dimethoxyphosphoryl)oxy]-4,4-difluorobut-3-enoate

Product 1

HCID 11528911ethyl 3-(diisopropylamino)-4,4-difluorobut-3-enoateYield 70.6%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Diisopropylamine (15.2 g, 0.15 mol) is added dropwise over 10 min to a solution of ethyl 3-[(dimethoxyphosphoryl)oxy]-4,4-difluorobut-3-enoate (IV-1) (14.2 g, 97%, 0.05 mol) in 100 ml methyl-tert-butyl ether. After 19 h heating under reflux the reaction mixture is cooled to room temperature, washed twice with 10 ml 10% sodium chloride solution each time, dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue was distilled for further use. 8.8 g (95%, 67.4% of theory) of ethyl 3-(diisopropylamino)-4,4-difluorobut-3-enoate are obtained (boiling point 55-57° C. at 0.5 hPa).

Workup

  1. temperatureAfter 19 h heating
  2. temperatureunder reflux the reaction mixture
  3. washwashed twice with 10 ml 10% sodium chloride solution each time
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. distillationThe residue was distilled for further use

Sources & evidence

ORD record
ord-385855a883774c868ae43bc64a47f5a5
Source dataset
uspto-grants-2009_09
Patent number
US07585998B2

Reaction notes

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