Trifluoroacetic acid → HCID 22080535, compound

HRID 1047832Notes

Reaction equation

HRID 1047832 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1([C:13]([OH:15])=[O:14])[C:10]([OH:12])=[O:11].F[C:17](F)(F)[C:18](O)=O>C(Cl)Cl>[CH2:17]([O:11][C:10]([C:2]1([C:13]([OH:15])=[O:14])[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1]1)=[O:12])[CH3:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 2519571,3-Dihydroindene-2,2-dicarboxylic acid

Product 1

HCID 22080535HCID 22080535, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 200 mL round bottom flask is charged with indan-2,2-dicarboxylic acid tent-butyl ester ethyl ester (8.69 g, 29.93 mmol). DCM (40 mL) and a stirring bar are added. Stirring is initiated. Trifluoroacetic acid (20.0 mL, 269 mmol) is added. After 20 h, tlc analysis (silica, 1:1 ethyl actetate:heptanes), indicates complete consumption of starting material. The reaction mixture is diluted with DCM (50 mL) and evaporated under reduced pressure. The resultant oil is diluted with DCM (55 mL) and evaporated under reduced pressure. The resultant oil is diluted with toluene (50 mL) and evaporated under reduced pressure by pumping to constant weight to give 6.78 g of white solid material.

Workup

  1. customconsumption of starting material
  2. additionThe reaction mixture is diluted with DCM (50 mL)
  3. customevaporated under reduced pressure
  4. additionThe resultant oil is diluted with DCM (55 mL)
  5. customevaporated under reduced pressure
  6. additionThe resultant oil is diluted with toluene (50 mL)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1d3a4debfbdd4671add4c3358639c907
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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