Methyl iodide → HCID 12994066, compound

HRID 1581755Notes

Reaction equation

[H-].[Na+].[CH3:3]I.[OH:5][C:6]1([C:12]2[CH:25]=[CH:24][C:23]3[C:14](=[C:15]4[C:20](=[CH:21][CH:22]=3)[CH:19]=[CH:18][CH:17]=[N:16]4)[N:13]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1>>[CH3:3][O:5][C:6]1([C:12]2[CH:25]=[CH:24][C:23]3[C:14](=[C:15]4[C:20](=[CH:21][CH:22]=3)[CH:19]=[CH:18][CH:17]=[N:16]4)[N:13]=2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 24758Sodium hydride

HCID 12994064HCID 12994064, compound

Product 1

HCID 12994066HCID 12994066, compoundYield 90%

Procedure

Through use of General Procedure II, NaH (0.110 g 4.6 mmol), methyl iodide (0.65 mL, 4.6 mmol), and 2-[(1-hydroxycyclohexyl)]-1,10-phenanthroline (0.320 g, 1.15 mmol), prepared as described by Example 1, were reacted to provide 0.301 g (90% yield) of the title methyl ether as a colorless oil: 1H NMR (300 MHz, CDCl3) δ9.24 (dd, J=4.50, 1.80 Hz, Hp9), 8.25 (d, J=8.40 Hz, Hp4, dd, J=8.10, 2.40 Hz, Hp7), 7.96 (d, J=8.40 Hz, Hp3), 7.82 and 7.75 (two d, J=8.80 Hz, Hp5 and Hp6), 7.61 (dd, J=8.10, 4.50 Hz, Hp8), 3.11 (s, 3H, OCH3), 2.23 (m, 4H, cyclohexyl H), 1.74 (m, 6H, cyclohexyl H); 13C NMR (75 MHz) δ166.33, 150.49, 146.33, 145.11, 136.40, 136.04, 128.77, 127.41, 126.38, 126.03, 122.40, 120.45, 80.46, 50.45, 33.83, 25.08, 21.69; IR (CHCl3) 3048 (C—H Ar), 2933 ((CH), 908 (C—H Ar), cm−1; HRMS m/e Calcd for C19H21N2O (MH+): 293.1654, found: 293.1665.

Workup

customwere reacted

Sources & evidence

ORD record: ord-3e1967e8d4f9472e986e465ac1334583
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06730788B1

Reaction notes

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