Tetrahydrofuran → 5-t-Butyldimethylsilyloxymethyl-1-[(2'-carbomethoxybiphenyl-4-yl)methyl]-4-chloro-2-(cis-pent-1-en-1-yl)imidazole

HRID 653935

Reaktionsgleichung

Reaktionsgleichung von HRID 653935
[Si:1]([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]=O)=[N:12][C:11]=1[Cl:34])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].[CH2:41]1[CH2:45]O[CH2:43][CH2:42]1>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CCC>[O:8]([CH2:9][C:10]1[N:14]([CH2:15][C:16]2[CH:17]=[CH:18][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:20][CH:21]=2)[C:13](/[CH:32]=[CH:45]\[CH2:41][CH2:42][CH3:43])=[N:12][C:11]=1[Cl:34])[Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 198154595-t-Butyldimethylsilyloxymethyl-1-[(2'-carbomethoxybiphenyl-4-yl)methyl]-4-chloroimidazole-2-carboxaldehydeHCID 23665647Potassium tert-butoxide

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 159628Butyltriphenylphosphonium bromideKatalysator

Versuchsvorschrift

5-t-Butyldimethylsilyloxymethyl-1-[(2'-carbomethoxybiphenyl-4-yl)methyl]-4-chloroimidazole-2-carboxaldehyde (200 mg) was added all at once to a solution of n-butyltriphenylphosphonium bromide (0.26 g) and potassium t-butoxide (70 mg) in THF at 0° C. The reaction mixture was stirred at room temperature for 15 minutes when it was quenched with saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate, the organic layers washed with water, dried (MgSO4) and the solvent removed in vacuo. The residue was flash chromatographed in hexane/ethyl acetate (5:1) to yield 100 mg of an oil. NMR (200 MHz, CDCl3) δ 7.85 (d, 1H), 7.54 (t, 1H), 7.42 (t, 1H), 7.35-7.24 (m, 3H), 7.07 (d, 2H), 6.07 (d, 1H), 5.87 (d of t, 1H), 5.28 (s, 2H), 4.59 (s, 2H), 3.64 (s, 3H), 2.69 (quart., 2H), 1.46 (sext., 2H), 0.91 (t, 3H), 0.86 (s, 9H), 0.05 (s, 6H).

Aufarbeitung

  1. customwas quenched with saturated aqueous ammonium chloride solution
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layers washed with water
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customchromatographed in hexane/ethyl acetate (5:1)

Quellen und Nachweise

ORD-Eintrag
ord-2f2d885fda374079bdbff7ae7c4dbbdd
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05128355

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