HCID 19004295, compound → HCID 19004535, compound

HRID 2225739Notes

Reaction equation

HRID 2225739 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][C:13]#[C:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:25])[C:22]([OH:24])=[O:23])=[CH:17][CH:16]=1>ClCCl.[Pd]>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([C:21](=[O:25])[C:22]([OH:24])=[O:23])=[CH:19][CH:20]=1

Participants

4

Reactant 1

HCID 19004295HCID 19004295, compound

Product 1

HCID 19004535HCID 19004535, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of 4-[3-(2-naphthalenyloxy)-1-propynyl]-alpha-oxobenzeneacetic acid (0.13 g) in dichloromethane (19 mL) was hydrogenated over 10 % palladium on carbon (0.016 g) at atmospheric pressure. The resulting mixture was filtered twice through a pad of celite to remove insoluble materials, then the tiltrate was evaporated and the residue was crystallized from ethyl acetate-hexane to afford 0.083 g of 4-[3-(2-naphthalenyloxy) propyl]-alpha-oxobenzeneacetic acid, mp 151°-154° C.

Workup

  1. filtrationThe resulting mixture was filtered twice through a pad of celite
  2. customto remove insoluble materials
  3. customthe tiltrate was evaporated
  4. customthe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-e5d1d59336f24845ad357861ecc05b44
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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