Sodium hydride → 5-(5,6,7,8-tetrahydro-naphthalen-2-yl)-1-(2-trimethylsilanyl ethoxymethyl)-1H-imidazole

HRID 983600Notes

Reaction equation

HRID 983600 reaction equation
[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:11]1[NH:15][CH:14]=[N:13][CH:12]=1.[H-].[Na+].[CH3:18][Si:19]([CH2:22][CH2:23][O:24][CH2:25]Cl)([CH3:21])[CH3:20]>>[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:11]1[N:15]([CH2:25][O:24][CH2:23][CH2:22][Si:19]([CH3:21])([CH3:20])[CH3:18])[CH:14]=[N:13][CH:12]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 220187485-(5,6,7,8-tetrahydro-naphthalen-2-yl)-1H-imidazole

Product 1

HCID 220185605-(5,6,7,8-tetrahydro-naphthalen-2-yl)-1-(2-trimethylsilanyl ethoxymethyl)-1H-imidazoleYield 52%

Procedure

Reaction of 5-(5,6,7,8-tetrahydro-naphthalen-2-yl)-1H-imidazole(387 mg, 1.95 mmol), NaH (60%, 76 mg, 1.89 mmol), and SEMCl (474 uL, 2.28 mmol) followed by column chromatography on silica gel (hexane/EtOAC 3:2) gave the title compound (321 mg, 52%) as a brown oil. 1H NMR (300 MHz, CDCl3) δ0.00 (s, 9H), 0.92 (t, 2H, J=9.0 Hz), 1.80-1.83 (m, 4H), 2.77-2.81 (m, 4H), 3.51 (t, 2H, J=9.0 Hz), 5.28 (s, 2H), 7.08 (d, 1H, J=9.0 Hz), 7.29 (s, 1H), 7.48 (d, 1H, J=6.0 H z), 7.54 (s, 1H), 7.61 (s, 1H).

Sources & evidence

ORD record
ord-aa1e63d127a742879b432d93b1786d03
Source dataset
uspto-grants-2005_03
Patent number
US06864265B2

Reaction notes

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