FIELD: chemistry.
SUBSTANCE: invention relates to a method for synthesis of optically active 3-alkyl-1-hydroxy-1'S-methylcyclopentanols of general formula R=n-C4H9, n-C5H11, n-C8H17, which can be used in fine organic synthesis. The disclosed method involves reaction of α-olefins of general formula RCH=CH2, where R=n-C4H9, n-C5H11, n-C8H17 with triethylaluminium (AlEt3) in the presence of a zirconocene dichloride (Cp2ZrCl2) catalyst in an argon atmosphere at room temperature and atmospheric pressure in hexane for 8 hours, with subsequent transfer of the reaction mass into an autoclave and addition of a copper chloride catalyst (CuCl) at -15°C and (S)-methyl ether of lactic acid (CH3CH(OH)CO2CH3) in molar ratio α-olefin: AlEt3 : Cp2ZrCl2 : CuCl : (CH3CH(OH)CO2CH3)= 10 : (20-24) : (0.3-0.7) : (0.8-1.2) : (10-14), stirring the reaction mass at 60°C for 6-8 hours and hydrolysis of the reaction mass.
EFFECT: high output of end product (36-57%).
1 tbl, 1 ex
Title | Year | Author | Number |
---|---|---|---|
METHOD FOR PRODUCTION OF 3-n-ALKYL-1-HYDROXYCYCLOPENTANE-n-ALKYLCARBOXYLATES | 2004 |
|
RU2307825C2 |
METHOD OF PREPARING 1-METHYL-3-ALKYLCYCLOPENTANE-1-OLS | 2002 |
|
RU2219157C1 |
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|
RU2173320C1 |
METHOD OF PREPARING TRANS-3,4-DIALKYLCYCLOPENTAN-1-OLS | 2003 |
|
RU2247705C2 |
METHOD FOR PRODUCTION OF 1,3,4-TRIALKYLCYCLOPENTANE-1-OLS | 2003 |
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METHOD OF COMBINED SYNTHESIS OF 1-ETHYL-3,6-DIALKYLCYCLOHEPTAOXALANES AND 1-ETHYL-3,5-DIALKYLCYCLOHEPTAOXALANES | 2001 |
|
RU2192423C1 |
METHOD FOR COMBINED PREPARING 1,1,3-TRIALKYL-1,5-PENTANEDIOLS AND 1,1,4-TRIALKYL-1,5-PENTANEDIOLS | 2002 |
|
RU2235711C2 |
METHOD OF PRODUCING 1-BROMO-3-ALKYLBOROLANES | 2012 |
|
RU2507208C1 |
METHOD FOR COMBINED SYNTHESIS OF 1-ETHYL-2-ALKYLIDENEALUMINACYCLOPENTANES AND 1-ETHYL-2-METHYLENE-3-ALKYLALUMINACYCLOPENTANES | 2009 |
|
RU2423370C2 |
METHOD OF PRODUCING 1-ETHYL-3-ALKYLALUMINIUM CYCLOPENTANES | 2009 |
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Authors
Dates
2010-09-27—Published
2008-02-19—Filed