http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1346289-A
Outgoing Links
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| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_6ccfe4f5e42f58f62f1d43a71ecf7fe2 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C49-493 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C49-395 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C49-517 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C45-676 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D317-72 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C45-59 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C49-523 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C11B9-003 |
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| filingDate | 1973-01-17-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1974-02-06-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-1346289-A |
| titleOfInvention | Cyclopentanone derivatives |
| abstract | 1346289 Cyclopentanone derivatives SOC ANON DES ETABS ROURE-BERTRAND FILS & JUSTIN DUPONT 17 Jan 1973 [18 Jan 1972] 2466/73 Heading C2C [Also in Division A5] The invention comprises compounds of the general Formula I in which R represents a hydrocarbon group having from 3 to 7 carbon atoms, X represents -CN, -CHO, -CH 2 OH, lower alkoxymethyl, lower alkanoyloxymethyl or lower alkylcarbonyl group and Y represents an oxo or ketal group, the lower alkyl moieties in which groups contain not more than 6 carbon atoms, provided that when X is CH 3 CO- and Y is = O, R is not n-pentyl. Compounds according to the invention having the Formula III may be prepared by condensing the corresponding cyclopent-2-en-I-ene with a lower alkylcyanoacetate to obtain a compound of Formula IV in which R<SP>3</SP> is a C 1 -C 4 alkyl group which gives the compound of Formula II on hydrolysis and decarboxylation. Compound II may be ketalized by reaction with a lower alkylene glycol, or mixed orthoformate thereof in the presence of and acid catalyst to give a compound V wherein R<SP>1</SP> and R<SP>2</SP> together represent Compounds VI according to the invention in which X is a formyl group may be prepared by reduction of V using, e.g. diisobutyl aluminium hydride and may be converted to the free ketone (VII) by reaction with excess acetone at elevated temperature. Compounds according to the invention having Formula VIII may be prepared by VI by reduction, e.g. using LiAlH 4 , diisobutylaluminium hydride/ pyridine or aluminium isopropylate/isopropanol and may be converted to the free ketone IX by conventional means. Compounds having Formula X in which Z is C 1 -C 6 alkyl or C 1 -C 6 alkylcarbonyl may be prepared by etherification of VIII by known means and may be converted to the free ketone XI again by known means Reaction of an appropriate cyclopent-2-en- 1-one with a compound of Formula XIV may be used to produce a compound of Formula XIII in which R<SP>4</SP> is a C 1 -C 6 alkyl group and R<SP>5</SP> is a C 1 -C 4 alkyl group which may be converted by hydrolysis and de. carboxylation into a compound of Formula XII. A number of particular compounds of Formula I are described and the following are claimed specifically. 3-Cyanomethyl-2-n-pentyl- 1 - cyclopentanone; 3 - cyanomethyl - 1,1- ethylenedioxy - 2 - n - pentyl - cyclopentane; 1,1 - ethylenedioxy - 3 formylmethyl - 2 - npentylcyclopentane; 3 - formylmethyl - 2 - npentyl - 1 - cyclopentanone; 1,1 - ethylenedioxy - 3 - hydroxyethyl - 2 - n - pentylcyclopentane; 3 - hydroxyethyl - 2 - n - pentyl - 1- cyclo - pentanone; 3 - acetoxyethyl - 1,1- ethylenedioxy - 2 - n - pentyl - cyclopentane; 3 - acetoxyethyl - 2 - n - pentyl - 1 - cyclopentanone and 2 - n - pentyl - 3 - propionylmethyl- 1-cyclopentanone. |
| priorityDate | 1972-01-18-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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