Methyl iodide → HCID 12994067, compound

HRID 1581756Notes

Reaction equation

HRID 1581756 reaction equation
[H-].[Na+].[CH3:3]I.[CH2:5]([C:7]([C:11]1[CH:24]=[CH:23][C:22]2[C:13](=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[CH:17][CH:16]=[N:15]3)[N:12]=1)([OH:10])[CH2:8][CH3:9])[CH3:6]>>[CH2:5]([C:7]([C:11]1[CH:24]=[CH:23][C:22]2[C:13](=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[CH:17][CH:16]=[N:15]3)[N:12]=1)([O:10][CH3:3])[CH2:8][CH3:9])[CH3:6]

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10264916HCID 10264916, compound

Product 1

HCID 12994067HCID 12994067, compoundYield 65%

Procedure

By using General Procedure II, NaH (0.035 g, 1.5 mmol), methyl iodide (0.092 mL, 1.5 mmol), and 2-[(1-ethyl-1-hydroxypropyl)]-1,10-phenanthroline (0.098 g, 0.368 mmol), prepared as described by Example 2, were reacted to yield 0.066 g (65% 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), 8.23 (dd, J=8.40, 1.80 Hz, Hp7), 8.20 (d, J=8.40 Hz, Hp4), 7.97 (d, J=8.40 Hz, Hp3), 7.78 and 7.72 (two d, J=8.80 Hz, Hp5 and Hp6), 7.60 (dd, J=7.80, 4.50 Hz, Hp8), 3.24 (s, OCH3), 2.34 and 2.24 (two dq, J=7.5 Hz, (CH2CH3)2), 0.73 (t, J=7.50 Hz, (CH2CH3)2); 13C NMR (75 MHz) δ164.85, 150.31, 146.45. 145.28, 136.10, 135.54, 128.89. 127.24, 126.55, 125.88, 122.48, 121.52, 84.26, 49.80, 28.17, 7.54; IR (CHCl3) 2969 (C—H Ar), 2935 (CH), 910 (C—H Ar) cm−1; HRMS m/e Calcd for C18H21N2O (MH+): 281.164, found, 281.1646.

Workup

  1. customprepared
  2. customwere reacted

Sources & evidence

ORD record
ord-960dec09ef904cec95ae9526a7fe6cf2
Source dataset
uspto-grants-2004_05
Patent number
US06730788B1

Reaction notes

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