Tetrahydrofuran → 1-[3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolyl-methoxy]phenyl]propyl]-2-imidazolemethanol

HRID 322387ノート

反応式

HRID 322387 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1(/[CH:13]=[CH:14]/[C:15]2[O:16][CH:17]=[C:18]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30][N:31]4[CH:35]=[CH:34][N:33]=[C:32]4[C:36](OCC)=[O:37])=[CH:24][CH:23]=3)[N:19]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O1CCCC1.[OH-].[Na+]>CCOCC.O>[C:7]1(/[CH:13]=[CH:14]/[C:15]2[O:16][CH:17]=[C:18]([CH2:20][O:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30][N:31]4[CH:35]=[CH:34][N:33]=[C:32]4[CH2:36][OH:37])=[CH:24][CH:23]=3)[N:19]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22009644ethyl 1-[3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]propyl]-2-imidazolecarboxylate

生成物 1

HCID 220098741-[3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolyl-methoxy]phenyl]propyl]-2-imidazolemethanol収率 58.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

To a suspension of lithium aluminum hydride (25 mg) in ether (5 ml) was added dropwise, under ice-cooling, a solution of ethyl 1-[3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]propyl]-2-imidazolecarboxylate (300 mg) in ether (5 mg)—tetrahydrofuran (10 ml). The mixture was stirred for one hour, to which was added 4N aqueous sodium hydroxide (0.025 ml). The mixture was stirred for 30 minutes at room temperature. The reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated to leave a crystalline product. Recrystallization from ethyl acetate-hexane gave 1-[3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolyl-methoxy]phenyl]propyl]-2-imidazolemethanol (160 mg, 58%) as colorless prisms, mp 143-144° C.

後処理

  1. additionwas added dropwise, under ice-
  2. temperaturecooling
  3. stirringThe mixture was stirred for 30 minutes at room temperature
  4. extractionwas subjected to extraction with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto leave a crystalline product
  9. customRecrystallization from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-55ee207eca8b4a35b7d5f9e003c3e8a4
出典データセット
uspto-grants-2001_04
特許番号
US06211215B1

反応ノート

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