![106685-41-0](/CAS/GIF/106685-41-0.gif)
Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate synthesis
- Product Name:Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate
- CAS Number:106685-41-0
- Molecular formula:C29H30O3
- Molecular Weight:426.55
![Adapalene](/CAS/GIF/106685-40-9.gif)
106685-40-9
608 suppliers
$6.00/50mg
![(TRIMETHYLSILYL)DIAZOMETHANE](/CAS/GIF/18107-18-1.gif)
18107-18-1
211 suppliers
$33.00/5g
![Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate](/CAS/GIF/106685-41-0.gif)
106685-41-0
167 suppliers
$21.00/100mg
Yield:106685-41-0 79%
Reaction Conditions:
in tetrahydrofuran;methanol at 0 - 20; for 1 h;
Steps:
1.5 Methyl 6-(3-(adamantan-l-yl)-4-methoxyphenyl)-2-naphthoate (5).
To a solution of adapalene (50 mg, 0.121 mmol) in 4: 1 THF/MeOH (0.4 mL) at 0 °C was added TMSCH2N2 (0.15 mL, 0.290 mmol) and the reaction was warmed to room temperature over 1 hour. The reaction mixture was concentrated, IN HCl was added, and was extracted with EtOAc 3x. The combined organic layers were washed with water and brine, dried over Na2S04, filtered, and concentrated; yielding the title compound as a white solid (41 mg, 79% yield). NMR (500 MHz, CDC13) δ 8.61 (s, 1H), 8.07 (dd, J = 8.6, 1.7 Hz, 1H), 8.03 - 7.96 (m, 2H), 7.92 (d, J = 8.6 Hz, 1H), 7.80 (dd, J = 8.5, 1.8 Hz, 1H), 7.60 (d, J = 2.4 Hz, 1H), 7.55 (dd, J = 8.4, 2.4 Hz, 1H), 7.00 (d, J = 8.5 Hz, 1H), 3.99 (s, 3H), 3.91 (s, 3H), 2.19 (s, 6H), 2.10 (s, 3H), 1.80 (s, 6H); 13C NMR (125 MHz, CDC13) δ 167.44, 159.03, 141.51, 139.11, 136.06, 132.67, 131.35, 130.95, 129.82, 128.33, 127.02, 126.59, 126.09, 125.84, 125.68, 124.84, 112.21, 55.27, 52.31, 40.72, 37.25, 29.23; HRMS Accurate mass (ES+): Found 427.2268, C29H3i03 (M+H+) requires 427.2273.
References:
AUSUBEL, Frederick M.;KIM, Wooseong;MYLONAKIS, Eleftherios;WUEST, William M. WO2018/213609, 2018, A1 Location in patent:Page/Page column 93
![Methyl 6-bromo-2-naphthoate](/CAS/GIF/33626-98-1.gif)
33626-98-1
324 suppliers
$16.80/1g
![1-(5-Bromo-2-methoxy-phenyl)adamantane](/CAS/GIF/104224-63-7.gif)
104224-63-7
311 suppliers
$16.00/5g
![Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate](/CAS/GIF/106685-41-0.gif)
106685-41-0
167 suppliers
$21.00/100mg
![Methyl 6-bromo-2-naphthoate](/CAS/GIF/33626-98-1.gif)
33626-98-1
324 suppliers
$16.80/1g
![1-(5-Bromo-2-methoxy-phenyl)adamantane](/CAS/GIF/104224-63-7.gif)
104224-63-7
311 suppliers
$16.00/5g
![2,2'-Bis-(1-adaMantyl)-4,4'-diMethoxybiphenyl](/CAS/GIF/932033-57-3.gif)
932033-57-3
60 suppliers
$130.00/50mg
![Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate](/CAS/GIF/106685-41-0.gif)
106685-41-0
167 suppliers
$21.00/100mg
![2-Naphthalenecarboxylic acid, 6-(4-hydroxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-, methyl ester](/CAS/20210305/GIF/106685-43-2.gif)
106685-43-2
0 suppliers
inquiry
![Iodomethane](/CAS/GIF/74-88-4.gif)
74-88-4
349 suppliers
$15.00/10g
![Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate](/CAS/GIF/106685-41-0.gif)
106685-41-0
167 suppliers
$21.00/100mg
![3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID](/CAS/GIF/459423-32-6.gif)
459423-32-6
91 suppliers
$50.00/25mg
![2-Naphthalenecarboxylic acid, 6-[(4-methylphenyl)sulfonyl]-, methyl ester](/CAS/20210305/GIF/366799-67-9.gif)
366799-67-9
0 suppliers
inquiry
![Mehtyl 6-[3-(1-adamanty)-4-methoxy phenyl]-2-naphthoate](/CAS/GIF/106685-41-0.gif)
106685-41-0
167 suppliers
$21.00/100mg