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

HRID 322387노트

반응식

HRID 322387 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-55ee207eca8b4a35b7d5f9e003c3e8a4
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211215B1

반응 노트

불러오는 중…