Water → HCID 90052092, compound

HRID 2284679Notes

Reaction equation

HRID 2284679 reaction equation
[F:1][C:2]([F:19])([CH:8](O)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(OCC)(=O)C.O.COCCN(S(F)(F)[F:37])CCOC>C(Cl)Cl>[F:1][C:2]([F:19])([CH:8]([F:37])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 90052104HCID 90052104, compound

Product 1

HCID 90052092HCID 90052092, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2,2-difluoro-3-hydroxy-3-(3-nitrophenyl)propanoate (C29, 1.02 g) in methylene chloride (22 mL), bis(2-methoxyethyl)aminosulfur trifluoride (1.6 mL) was added under ice cooling, and the mixture was stirred at room temperature for 16 hours. To the reaction mixture, ethyl acetate and water were added. The organic layer was separated, washed successively with 1.0 mol/L aqueous hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain ethyl 2,2,3-trifluoro-3-(3-nitrophenyl)propanoate (C30, 1.19 g).

Workup

  1. customThe organic layer was separated
  2. washwashed successively with 1.0 mol/L aqueous hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-946be7b213dc4da780e24a26bc07951d
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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