2-Ethyl-2-adamantanol synthesis
- Product Name:2-Ethyl-2-adamantanol
- CAS Number:14648-57-8
- Molecular formula:C12H20O
- Molecular Weight:180.29
700-58-3
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811-49-4
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14648-57-8
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Yield:14648-57-8 94%
Reaction Conditions:
in tetrahydrofuran;benzene at 0;
Steps:
2-Ethyl-tricyclo[3.3.1.1(3,7)]decan-2-amine 9d.
Tertiary alcohol 9b was obtained after treating a solution of adamantanone (5a)(500 mg, 3.33 mmol) in dry THF (30% solution w/v) with n-ethyllithium(0.5M in benzene), (20 mL, 10,0 mmol) at 0 C and stirringthe mixture overnight; yield 560 mg (94%); 1H NMR (CDCl3, 400 MHz): d (ppm) 0.86 (t, J 7.0 Hz, CH2CH3), 1.40e1.70 (m, 10 H,1,3, 4eq,9eq,6,8eq, 10eq adamantane-H, CH2CH3), 1.75e1.83 (m, 2H,5,7 adamantane-H),1.94 (d, J 12.1 Hz, 2H, 8ax, 10ax adamantane-H), 2.07 (d, J 12.1 Hz, 2H, 4ax, 9ax adamantane-H); 13C NMR(CDCl3, 50 MHz) d (ppm) 6.4 (CH2CH3), 27.4, 27.5 (5,7 adamantane-C), 30.6 (CH2CH3), 33.0 (8,10 adamantane -C), 34.6 (4,9adamantane-C), 36.6 (1,3 adamantane-C), 38.5 (6 adamantane-C),74.9 (2 adamantane-C).
References:
Tzitzoglaki, Christina;Drakopoulos, Antonios;Konstantinidi, Athina;Stylianakis, Ioannis;Stampolaki, Marianna;Kolocouris, Antonios [Tetrahedron,2019,vol. 75,# 34,art. no. 130408]
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14648-57-8
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14648-57-8
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