ChemicalBook CAS DataBase List 5,6,7,7a-Tetrahydro-5-(triphenylmethyl)thieno[3,2-c]pyridinone

5,6,7,7a-Tetrahydro-5-(triphenylmethyl)thieno[3,2-c]pyridinone synthesis

7synthesis methods

Product Name:5,6,7,7a-Tetrahydro-5-(triphenylmethyl)thieno[3,2-c]pyridinone
CAS Number:109904-26-9
Molecular formula:C26H23NOS
Molecular Weight:397.53

4,5,6,7-Tetrahydro-5-(triphenylmethyl)thieno[3,2-c]pyridine

109904-25-8
50 suppliers
$290.00/50 mg

5,6,7,7a-Tetrahydro-5-(triphenylmethyl)thieno[3,2-c]pyridinone

109904-26-9
104 suppliers
$70.00/25mg

Yield: 99%

Reaction Conditions:

Stage #1:N-trityl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine with n-butyllithium in tetrahydrofuran;hexane;toluene at -5 - 10;
Stage #2: with Trimethyl borate in tetrahydrofuran;hexane;toluene at -5 - 10;
Stage #3: with water;dihydrogen peroxide in tetrahydrofuran;hexane;tolueneProduct distribution / selectivity;

Steps:

7.A
Method AIn a 5 ltr 4-necked flask equipped with a thermometer and mechanical stirrer, (246 ml, 0.39 moles) n-butyl lithium (1.6 mole solution in hexane) was added to a solution of 5- Triphenyl methyl-tetrahydro-4,5,6,7- thieno-[3,2-c] -pyridine (100 g, 0.26 moles) was added at -5 +/-5 °C in a mixture of tetrahydrofuran and toluene (700 ml; 2:5). Stir the reaction mass for 1 to 2 hrs at 10 +/-2 °C. Cool the mass to -5 +/-5 °C. Slowly add a solution trimethyl borate (60 g, 0.58 moles) in toluene (100 ml) to the reaction mass and stir for 1 to 2 hrs at 10 +/-2 °C. Reaction mass was quenched by adding hydrogen peroxide and water. Product extract with toluene (2 x 200 ml), organic layer washed with sodium chloride solution then water and dried over sodium sulfate. Recover the solvent under vacuum and crystalise the product in diisopropyl ether, methanol or mixture thereof. Filter the product and slurry wash with diisopropyl ether, methanol or mixture thereof. Dry the material under vacuum at 30 to 40 °C to obtain 5-Triphenyl methyl-tetrahydro-5, 6, 7,7a 4H- thieno-[3,2-c]-pyridone-2 (80 g, 99%).

References:

MAYUKA LABS PVT. LTD.;KRISHNAMURTHY, Chandra, Sekhar, Nakka;SINGH, Jagat;KHAN, Mohd, Yunus WO2012/1486, 2012, A1 Location in patent:Page/Page column 19

109904-25-8
50 suppliers
$290.00/50 mg