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

HRID 465846

反応式

HRID 465846 の反応式
[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>[Si:1]([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])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 159628Butyltriphenylphosphonium bromide触媒

実験手順

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) δ7.85 (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).

後処理

  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)

出典と根拠

ORDレコード
ord-2c5033773bcf4ba782255fe092162140
出典データセット
uspto-grants-1992_10
特許番号
US05153197

関連ノート

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