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

HRID 862760Notes

Reaction equation

HRID 862760 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]([OH:22])=[O:21])O)=[CH:11][CH:10]=1>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 232935722-(6-Fluoro-1-hydroxy-1-indanyl)acetic acid

Product 1

HCID 70130971(E)-2-(6-fluoro-1-indanylidene)acetic acidYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (100 mL) was added to a stirred, chilled (ice-methanol bath) solution of 2-(6-Fluoro-1-hydroxy-1-indanyl)acetic acid (37.5 g, 0.18 mol) in dichloromethane (900 mL). After 15 min, the mixture was concentrated in vacuo to give (E)-2-(6-fluoro-1-indanylidene)acetic acid as a yellowish-tan solid (33.0 g, 95%), m.p., 203°-205° C.; NMR (DMSO-d6): d 12.05 (br s, 1H, COOH), 7.16-7.65 (m, 3H, Ar), 6.37 (t,1H, =CH), 2.94-2.98, 3.15-3.20 (2m's, 4H, 2XCH2); steady-state nOe:irradiation at 6.37 d, observed 24% nOe at 7.65 d.

Workup

  1. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-35ba123dc7b64b5ea35be3b231624f6e
Source dataset
uspto-grants-1998_02
Patent number
US05719186

Reaction notes

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