1-Indanone → Indene

HRID 1110444Notes

Reaction equation

HRID 1110444 reaction equation
[C:1]1(=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C[Li]>CCOCC>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 67351-IndanoneHCID 178418348HCID 178418348, compound

Product 1

HCID 7219Indene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Starting indanones J may be synthesized from commercially available 1-indanone F, shown by the following reaction sequence, by initial formation of the tosyl hydrazone (H2NNHTs, 1:1 eq./EtOH, 100° until solubilized) followed by methyllithium-induced elimination (3 eq./Et2O, 25°, 2.5 hours) to give indene G. Hydroboration-oxidation of G using standard conditions affords 1,2-oxygen transposition product H. Dess-Martin periodinane oxidation affords desired indanone J. Indanone J is converted in good yield to corresponding compounds of the invention as described hereinbefore. ##STR7##

Workup

  1. customshown by the following reaction sequence

Sources & evidence

ORD record
ord-879874732201420189bdf54d2b90052d
Source dataset
uspto-grants-1990_12
Patent number
US04975461

Reaction notes

Loading…