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ChemicalBook CAS DataBase List 6-Methoxyphenazin-1-ol
13129-58-3

6-Methoxyphenazin-1-ol synthesis

6synthesis methods
-

Yield:13129-58-3 24%

Reaction Conditions:

with 18-crown-6 ether;potassium carbonate in N,N-dimethyl-formamide at 0;

Steps:

4.1.8. 1-Hydroxy-6-methoxyphenazine (14)

MeI (0.11 mL, 1.82 mmol) was added dropwise to a stirring solution of 1,6-dihydroxyphenazine (10) (350 mg, 1.65 mmol), K2CO3 (228 mg, 1.65 mmol) and 18-Crown-6 (436 mg, 1.65 mmol) in anhydrous DMF (22 mL) at 0 °C. Resulting mixture was left stirring overnight gradually reaching rt concentrated in vacuo. The resulting crude redissolved in 40 mL of EtOAc and the organic layer was extracted with 10% NaOH aqueous solution (4 30 mL to separate 1-hydroxy-6-methoxy phenazine from the di-methylated byproduct 9). Basic aqueous fractions were pooled and adjusted to pH 7 by 2 M HCl. The neutral aqueous layer was there after extracted by EtOAc (4x30 mL). Organic phases pooled, washed with brine (3 200 mL), dried over MgSO4 and concentrated in vacuo. The resulting crude was purified by flash column chromatography(10-50% EtOAc/Heptane) affording 89 mg (24%) of yellow solid. Rf: 0.33 (1:1 EtOAc/Heptane). 1H NMR (400 MHz,CDCl3) d 8.19 (s, 1H), 7.94 (dd, J = 8.9, 1.2 Hz, 1H), 7.82 (dd,J = 8.9, 1.2 Hz, 1H), 7.75 (dd, J = 8.9, 7.5 Hz, 2H), 7.29-7.22 (m,1H), 7.10 (dd, J = 7.5, 1.2 Hz, 1H), 4.19 (s, 3H). 13C NMR(101 MHz, CDCl3) d 155.3, 151.5, 142.7, 142.0, 137.7, 134.7,131.6, 130.7, 121.0, 120.7, 109.5, 107.0, 56.7. 1H og 13C NMR dataare in accordance with litterature.

References:

Viktorsson, Elvar ?rn;Melling Gr?the, Bendik;Aesoy, Reidun;Sabir, Misbah;Snellingen, Simen;Prandina, Anthony;H?gmoen ?strand, Ove Alexander;Bonge-Hansen, Tore;D?skeland, Stein Ove;Herfindal, Lars;Rongved, P?l [Bioorganic and Medicinal Chemistry,2017,vol. 25,# 7,p. 2285 - 2293]