2-(4,6-Difluoro-1-hydroxy-1-indanyl)acetic acid → (E)-2-(5-fluoro-1-indanylidene)acetic acid

HRID 1954879Notes

Reaction equation

HRID 1954879 reaction equation
F[C:2]1[CH:10]=[C:9](F)[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5]/[C:6]/2=[CH:12]\[C:13]([OH:15])=[O:14].[F:16]C1C=C(F)C=C2C=1CCC2(CC(O)=O)O>>[F:16][C:10]1[CH:2]=[C:3]2[C:7](=[CH:8][CH:9]=1)/[C:6](=[CH:12]/[C:13]([OH:15])=[O:14])/[CH2:5][CH2:4]2

Participants

3

Reactant 2

HCID 109112982-(4,6-Difluoro-1-hydroxy-1-indanyl)acetic acidHCID 10976722(E)-2-(4,6-difluoro-1-indanylidene)acetic acid

Product 1

HCID 23293571(E)-2-(5-fluoro-1-indanylidene)acetic acidYield 68%

Procedure

This compound was prepared in an analogous manner to (E)-2-(4,6-difluoro-1-indanylidene)acetic acid in Example 5e by substituting 2-(5-fluoro-1-hydroxy-1-indanyl)acetic acid (14.70 g, 0.069 mol) for 2-(4,6-difluoro-1-hydroxy-1-indanyl)acetic acid. Recrystallization from acetonitrile:2-propanol mixtures gave 9.05 g (68%) of (E)-2-(5-fluoro-1-indanylidene)acetic acid as a white solid: m.p., 240-242° C.;

Workup

  1. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-05fc2001735044d1aec9493e4e712de6
Source dataset
uspto-grants-2000_09
Patent number
US06124284

Reaction notes

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