Methyl iodide → HCID 22005076, compound

HRID 324878Notes

Reaction equation

[OH:1][CH2:2][C:3]1[C:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:6]([CH2:21][O:22][Si:23]([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:5]([CH:40]([CH3:42])[CH3:41])[N:4]=1.[CH3:43]I.[H-].[Na+]>O1CCCC1.O>[CH3:43][O:1][CH2:2][C:3]1[C:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[C:6]([CH2:21][O:22][Si:23]([C:36]([CH3:39])([CH3:38])[CH3:37])([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:5]([CH:40]([CH3:41])[CH3:42])[N:4]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of the intermediate obtained in Example 200, Step B (0.1 g, 0.17 mmol), methyl iodide (0.013 mL, 1.2 equiv), and sodium hydride (8 mg of a 60% dispersion in mineral oil, 1.2 equiv) in tetrahydrofuran (1 mL) was heated at 40° C. for 3 h. The mixture was diluted with water and extracted with ethyl acetate (3×10 mL). The combined organic phase was washed with saturated aqueous sodium chloride solution (3×10 mL). Silica gel chromatography provided a colorless solid (40 mg, 40%). 1H NMR (300 MHz, CDCl3): δ 7.41 (m, 6H), 7.32 (m, 4H), 7.06 (m, 4H), 4.62 (s, 2H), 4.27 (s, 2H), 3.48 (s, 3H), 3.15 (sept, 6.6 Hz, 1H), 2.36 (m, 2H), 1.27 (m, 2H), 1.18 (d, 6.6 Hz, 6H), 1.12 (m, 2H), 1.00 (s, 9H), 0.87 (m, 2H), 0.78 (t, 6.6 Hz, 3H).

Workup

extractionextracted with ethyl acetate (3×10 mL)
washThe combined organic phase was washed with saturated aqueous sodium chloride solution (3×10 mL)

Sources & evidence

ORD record: ord-329d7d28b39d4c0990bab7bd39fe81d6
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06218431B1

Reaction notes

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