Cyanoacetic acid → Hydroxyindene-3-acetic acid

HRID 484240

Reaction equation

HRID 484240 reaction equation
O[CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:11].C([CH2:14][C:15]([OH:17])=[O:16])#N>>[OH:11][CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10]([CH2:14][C:15]([OH:17])=[O:16])=[CH:2]1

Participants

3

Reactant 2

HCID 9740Cyanoacetic acidHCID 30140171H-Inden-1-one, 2,3-dihydro-2-hydroxy-

Product 1

HCID 19935709Hydroxyindene-3-acetic acid

Procedure

In an alternative preparation scheme, the intermediate hydroxyindanone can be reacted with cyanoacetic acid to give the corresponding hydroxyindene-3-acetic acid, which is then esterified before introduction of the R5 -methylene grouping in order to facilitate the purification of desired intermediates. Since introduction of the R5 -methylene grouping is accompanied by ester hydrolysis, the intermediate free acid is re-esterified to facilitate purification followed by reaction with an appropriate haloalkyl-A group to yield the desired final product ##STR20## can be prepared by reacting a halo-indene-3-acetic acid with a A(CH2)n -containing benzaldehyde prepared from the corresponding individual components ##STR21##

Workup

  1. customIn an alternative preparation scheme

Sources & evidence

ORD record
ord-89349e81815545f2859e8bf5621a76dd
Source dataset
uspto-grants-1993_07
Patent number
US05229516

Linked notes

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