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

HRID 862759Notes

Reaction equation

HRID 862759 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-a9c0a3bbdec346c38fe140bf4a089175
Source dataset
uspto-grants-1998_02
Patent number
US05719186

Reaction notes

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