2-Ethyl-1-decanol synthesis
- Product Name:2-Ethyl-1-decanol
- CAS Number:21078-65-9
- Molecular formula:C12H26O
- Molecular Weight:186.33
872-05-9
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97-93-8
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![Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-](/CAS/20210305/GIF/1000210-73-0.gif)
1000210-73-0
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Yield: 26 % ee
Reaction Conditions:
Stage #1:1-Decene;triethylaluminum with (p-S)(p-S)-bis[η5-[1-[(1S,2S,5R)-2-isopropyl-5-methylcyclohexyl]indenyl]]zirconium dichloride in hexane at 22; for 24 h;Inert atmosphere;Schlenk technique;
Stage #2: with oxygen in hexane at 0; for 26 h;
Stage #3: with hydrogenchloride;water in hexane at 0;enantioselective reaction;
Steps:
5.1 Reaction of terminal alkenes with AlEt3 in the presence of complexes 1 or 2
General procedure: A 10 ml flask equipped with a magnetic stirrer and filled with argon was loaded with 0.02-0.075 mmol of complexes 1 or 2, 3 ml of a solvent (benzene, hexane, cyclohexane), 1 mmol of alkenes (3a-g) and 1.2 mmol of AlEt3. The reaction mixture was stirred for 24 h at 22 °C. Then, a part of the reaction mixture was decomposed with 10% HCl or DCl at 0 °C. The products were extracted with benzene; further, the organic layer was dried over Na2SO4 and analyzed by GC or GC-MS. Another part of the reaction mixture was cooled to 0 °C and a dry oxygen was passed through for 2 h. The resultant mixture was further stirred under oxygen atmosphere for 24 h, and then treated with 10% HCl and extracted with Et2O. The organic layer was dried over Na2SO4, filtered, and concentrated. Alcohols 7a-g were separated by column chromatography. The chromatography of the mixture 7 + 8 on silica gel (hexane/Et2O 4:1) provided compound 8; then the column was washed with acetone to give 7a-g as a colorless oils. The organic fractions were concentrated and dried over Na2SO4. MTPA esters of 7a-g were prepared as described in Ref. [6] PSPA esters of 7a-g were prepared according to Ref. [7].
References:
Parfenova, Lyudmila V.;Kovyazin, Pavel V.;Tyumkina, Tatyana V.;Berestova, Tatyana V.;Khalilov, Leonard M.;Dzhemilev, Usein M. [Journal of Organometallic Chemistry,2013,vol. 723,p. 19 - 25]
872-05-9
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71526-27-7
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112-30-1
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872-05-9
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2386-64-3
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