ChemicalBook CAS DataBase List 2,2':6',2''-Terpyridine-4'-methanol

2,2':6',2''-Terpyridine-4'-methanol synthesis

5synthesis methods

Product Name:2,2':6',2''-Terpyridine-4'-methanol
CAS Number:148332-32-5
Molecular formula:C16H13N3O
Molecular Weight:263.29

247058-06-6 Synthesis

METHYL 2,2':6',2''-TERPYRIDINE-4'-CARBOXYLATE

247058-06-6
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148332-32-5
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Yield:148332-32-5 96%

Reaction Conditions:

with sodium tetrahydroborate;lithium chloride in ethanol; for 4 h;Reflux;

Steps:

[2,2':6',2''-Terpyridin]-4'-ylmethanol (7)

Compound 7 (3.90g, 13.4 mmol) was dispersed in 150 ml of ethanol. NaBH₄ (1.52 g, 40.2 mmol) and LiCl(1.70 g, 40.2 mmol) were added and the resulting mixture was heated to reflux for 4 h. After cooling to room temperature the solvent was removed under redcued pressure. 50 ml of water were added to the residue and the resulting slurry was extracted with DCM (3 x 40 ml). The combined organic phases were dried over Na₂SO₄ and the solvent was removed under reduced pressure. The product was obtained as a white powder. Yield:3.38 g (96%)mp:126-127°C;¹H-NMR(500 MHz, DMSO-d₆): δ 8.71 (ddd, J= 4.7 Hz, 1.7 Hz, 0.9 Hz, 2H), 8.63 (dt, J= 7.9 Hz, 1.0 Hz, 2H), 8.43 (s, 2H), 8.00 (td, J = 7.6 Hz, 1.8 Hz, 2H), 7.49 (ddd, J = 7.5 Hz, 4.7 Hz, 1.1 Hz, 2H), 5.59 (t, J = 5.9 Hz, 1H), 4.74 (d, J= 7.5 Hz, 2H)¹³C-NMR (126 MHz, DMSO-d₆): δ165.0, 156.1, 154.0, 149.5, 139.3, 137.6, 124.9, 120.9, 119.3, 52.9HRMS (ESI, m/z): calcd for C₁₆H₁₄N₃O [M+H]⁺: 264.1131; Found: 264.1132.