Trifluoroacetic acid → HCID 22184567, compound

HRID 494751Notes

Reaction equation

HRID 494751 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:11][C:12]([C:26]([O:28][CH2:29][CH3:30])=[O:27])([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:13][C:14]([O:16]C(C)(C)C)=[O:15])[CH:6]=[CH:7][C:8]=1[CH2:9][CH3:10])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:11][C:12]([C:26]([O:28][CH2:29][CH3:30])=[O:27])([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:13][C:14]([OH:16])=[O:15])[CH:6]=[CH:7][C:8]=1[CH2:9][CH3:10])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68580131HCID 68580131, compound2×

Product 1

HCID 22184567HCID 22184567, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 20.30 g (48.27 mmol) tert. butyl 4-(3,4-diethyl-phenyl)-3,3-bis-ethoxycarbonyl-butyrate (Intermediate product 61) in 100 mL CH2Cl2 was added 40 mL TFA while cooling with ice and the mixture was refluxed for 1 hour. The reaction mixture was evaporated down i. vac., the residue was combined with water and the aqueous phase exhaustively extracted with EtOAc. The combined org. extracts were washed with sat. aqueous NaCl solution, dried over sodium sulphate and evaporated i. vac.

Workup

  1. temperaturewhile cooling with ice
  2. temperaturethe mixture was refluxed for 1 hour
  3. customThe reaction mixture was evaporated down i
  4. extractionthe aqueous phase exhaustively extracted with EtOAc
  5. washextracts were washed with sat. aqueous NaCl solution
  6. dry with materialdried over sodium sulphate
  7. customevaporated i

Sources & evidence

ORD record
ord-dff8d536fe304aa49c97bb1060db9475
Source dataset
uspto-grants-2009_05
Patent number
US07538115B2

Reaction notes

Loading…