Dimethylformamide → 5-(5,6,7,8-Tetrahydro-naphthalen-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbaldehyde

HRID 7115Notes

Reaction equation

HRID 7115 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[N:15]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:14]=[N:13][CH:12]=1.[Li]CCCC.CN([CH:32]=[O:33])C>>[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]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:14]([CH:32]=[O:33])=[N:13][CH:12]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 220185605-(5,6,7,8-tetrahydro-naphthalen-2-yl)-1-(2-trimethylsilanyl ethoxymethyl)-1H-imidazoleHCID 178418339Butyllithium

Product 1

HCID 220185335-(5,6,7,8-Tetrahydro-naphthalen-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbaldehydeYield 57%

Procedure

Reaction of 5-(5,6,7,8-tetrahydro-naphthalen-2-yl)-1-(2-trimethylsilanyl ethoxymethyl)-1H-imidazole (268 mg, 0.82 mmol), 2.5 M n-BuLi (424 uL, 1.06 mmol), and DMF (253 uL, 3.27 mmol) for 2 h at −40° C. followed by column chromatography on silica gel (EtOAc/hexane 9:1) gave the title compound (166 mg, 57%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 0.00 (s, 9H), 0.94 (t, 2H, J=7.5 Hz), 1.80–1.85 (m, 4H), 2.80–2.83 (m, 4H), 3.60 (t, 2H, J=9.0 Hz), 5.81 (s, 2H), 7.13 (d, 1H, J=6.0 Hz), 7.51 (d, 1H, J=6.0 Hz), 7.57 (s, 1H), 7.60 (s, 1H). 9.88 (s, 1H).

Sources & evidence

ORD record
ord-8cca7825779048e586da57d8d41dcd5a
Source dataset
uspto-grants-2006_08
Patent number
US07084155B2

Reaction notes

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