Hydrochloric Acid → HCID 90052104, compound

HRID 2284678Notes

Reaction equation

HRID 2284678 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[O:8])([O-:3])=[O:2].C(OCC)(=O)C.Cl.Br[C:20]([F:27])([F:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>O1CCCC1.C[Si](Cl)(C)C.[Zn]>[F:26][C:20]([F:27])([CH:7]([OH:8])[C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 74493-NitrobenzaldehydeHCID 8857Ethyl AcetateHCID 69585Ethyl bromodifluoroacetate

Product 1

HCID 90052104HCID 90052104, compound

Reagents, catalysts & solvents 3

HCID 6397ChlorotrimethylsilaneCatalystHCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of zinc (962 mg) in tetrahydrofuran (25 mL), trimethylsilyl chloride (1 drop) and ethyl bromodifluoroacetate (2.2 mL) were added at room temperature, and the mixture was stirred for 5 minutes under reflux by heating. To the reaction mixture, 3-nitrobenzaldehyde (695 mg) was added, and the mixture was stirred for 30 minutes under reflux by heating. The reaction mixture was cooled to room temperature, and then ethyl acetate and 1.0 mol/L aqueous hydrochloric acid were added to the mixture. The organic layer was separated, washed successively with 1.0 mol/L aqueous hydrochloric acid and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 100 to 60% hexane in ethyl acetate) to obtain ethyl 2,2-difluoro-3-hydroxy-3-(3-nitrophenyl)propanoate (C29, 1.02 g).

Workup

  1. additionwere added at room temperature
  2. temperatureunder reflux
  3. temperatureby heating
  4. stirringthe mixture was stirred for 30 minutes
  5. temperatureunder reflux
  6. temperatureby heating
  7. customThe organic layer was separated
  8. washwashed successively with 1.0 mol/L aqueous hydrochloric acid and saturated aqueous sodium chloride
  9. dry with materialdried over anhydrous sodium sulfate
  10. customthe solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography (eluent, 100 to 60% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-129c83c2f70c442eb9acc2bc2872f0b6
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

Loading…