反応式
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].C([Li])CCC.CCCCCC.[CH2:39]([C:43]1[N:44]([CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=2[Cl:57])[C:45]([CH:48]=O)=[CH:46][N:47]=1)[CH2:40][CH2:41][CH3:42]>O1CCCC1.O>[CH2:39]([C:43]1[N:44]([CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=2[Cl:57])[C:45]([CH2:48][CH:8]=[CH:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3])=[CH:46][N:47]=1)[CH2:40][CH2:41][CH3:42]参加物
反応条件
- 温度
- 0 °C
実験手順
To a suspension of (4-carboxybutyl)triphenyl-phosphonium bromide (1.04 g, 2.35 mmol) in dry tetrahydrofuran (25 mL) at 0° C. under argon was added n-butyl lithium in hexane (1.8 mL of 2.5M, 4.6 mmol). The reaction mixture was stirred for 15 minutes at 0° C. and then a solution of 2-n-butyl-1-(2-chlorophenyl)methyl-1H-imidazol-5-carboxaldehyde [Example 6 (iii)] (0.5 g, 1.81 mmol) in tetrahydrofuran (25 mL) was added dropwise. The mixture was stirred an additional hour at 0° C. and then at ambient temperature for 3 days. Water was added and the mixture was extracted with diethyl ether. The aqueous layer was acidified to pH 3 with aqueous hydrochloric acid solution. The product was extracted into ethyl acetate, washed with water, dried, concentrated, and chromatographed over silica gel eluting with 5-10% methanol in methylene chloride to give 0.24 g of 6-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-4-hexenoic acid.
後処理
- stirringThe mixture was stirred an additional hour at 0° C.
- waitat ambient temperature for 3 days
- extractionthe mixture was extracted with diethyl ether
- extractionThe product was extracted into ethyl acetate
- washwashed with water
- customdried
- concentrationconcentrated
- customchromatographed over silica gel eluting with 5-10% methanol in methylene chloride
出典と根拠
- ORDレコード
- ord-f292aa281dd543869c402cc2b082136b
- 出典データセット
- uspto-grants-1996_06
- 特許番号
- US05530017
関連ノート
読み込み中…