Trifluoroacetic acid → (E)-2-(6-fluoro-1-indanylidene)acetic acid

HRID 362810Notes

Reaction equation

HRID 362810 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][CH2:14][C:15]2([CH2:19][C:20]([O-:22])=[O:21])O)=[CH:11][CH:10]=1.[Li+]>ClCCl>[F:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][CH2:14]/[C:15]/2=[CH:19]\[C:20]([OH:22])=[O:21])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23678141Lithium 2-(6-fluoro-1-hydroxy-1-indanyl)acetate

Product 1

HCID 70130971(E)-2-(6-fluoro-1-indanylidene)acetic acidYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.5 mL) was added to a stirred, chilled (ice-methanol bath) suspension of lithium 2-(6-fluoro-1-hydroxy-1-indanyl)acetate (0.5 g, 2.3 mmol) in dichloromethane (13.5 mL). After 15 min, the mixture was concentrated in vacuo and the resulting white solid was recrystallized from aqueous acetone to give (E)-2-(6-fluoro-1-indanylidene)acetic acid as white crystals (0.32 g, 73%) identical to compound of Example 1i by mixed m.p., (203°-205° C.) and NMR;

Workup

  1. temperaturechilled
  2. concentrationthe mixture was concentrated in vacuo
  3. customthe resulting white solid was recrystallized from aqueous acetone

Sources & evidence

ORD record
ord-81319226dcc44d8a9a659ad33e62c005
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

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