Fluoride Ion → 1-[(2'-Carbomethoxybiphenyl-4-yl)methyl]-4-chloro-5-hydroxymethyl-2-(cis-pent-1-en-1-yl)imidazole

HRID 847100

Reaction equation

HRID 847100 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]([O:30][CH3:31])=[O:29])=[CH:18][CH:17]=2)[C:13](/[CH:32]=[CH:33]\[CH2:34][CH2:35][CH3:36])=[N:12][C:11]=1[Cl:37])(C(C)(C)C)(C)C.[F-]>CCCCCC.C(OCC)(=O)C>[C:28]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:14]2[C:10]([CH2:9][OH:8])=[C:11]([Cl:37])[N:12]=[C:13]2/[CH:32]=[CH:33]\[CH2:34][CH2:35][CH3:36])=[CH:17][CH:18]=1)([O:30][CH3:31])=[O:29]

Participants

4

Reactant 2

HCID 28179Fluoride IonHCID 665771855-t-Butyldimethylsilyloxymethyl-1-[(2'-carbomethoxybiphenyl-4-yl)methyl]-4-chloro-2-(cis-pent-1-en-1-yl)imidazole

Product 1

HCID 665771821-[(2'-Carbomethoxybiphenyl-4-yl)methyl]-4-chloro-5-hydroxymethyl-2-(cis-pent-1-en-1-yl)imidazole

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

5-t-Butyldimethylsilyloxymethyl-1-[(2'-carbomethoxybiphenyl-4-yl)methyl]-4-chloro-2-(cis-pent-1-en-1-yl)imidazole (100 mg) was desilylated with fluoride by procedures familiar to one skilled in the art. Flash chromatography in 1:1 hexane/ethyl acetate yielded 65 mg of a viscous, colorless oil. NMR (200 MHz, CDCl3) δ7.85 (d, 1H), 7.55 (t, 1H), 7.42 (t, 1H), 7.28 (m, 3H), 7.05 (d, 2H), 6.11 (d, 1H), 5.92 (d of t, 1H), 5.30 (s, 2H), 4.57 (d, 2H), 3.64 (s, 3H), 2.69 (quart., 2H), 1.62 (t, 1H), 1.47 (sext., 2H), 0.92 (t, 1H).

Sources & evidence

ORD record
ord-6cfd174f3d74429aa9b8ca6571fb5b56
Source dataset
uspto-grants-1992_08
Patent number
US05138069

Linked notes

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