Potassium Sodium Tartrate → 5-(3-Hydroxypropyl)-1-methyl-2-ethylimidazole

HRID 863591

반응식

HRID 863591 반응식
[CH3:1][N:2]1[C:6]([CH2:7][CH2:8][C:9](OCC)=[O:10])=[CH:5][N:4]=[C:3]1[CH2:14][CH3:15].[H-].[H-].[H-].[H-].[Li+].[Al+3].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1>[OH:10][CH2:9][CH2:8][CH2:7][C:6]1[N:2]([CH3:1])[C:3]([CH2:14][CH3:15])=[N:4][CH:5]=1

참가 물질

5

반응물 3

HCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 22103420Ethyl 3-(1-methyl-2-ethylimidazol-5-yl)propionate

생성물 1

HCID 221034045-(3-Hydroxypropyl)-1-methyl-2-ethylimidazole수율 90.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

To a cooled (0° C.) solution of ethyl 3-(1-methyl-2-ethyl-imidazol-5-yl)propionate (1.75 g, 8.33 mmol) in 30 ml of THF was added 4.6 ml (4.6 mmol) of 1M LAH solution in THF at 0° C. After stirring at 0° C. for 15 min, the mixture was allowed to warm and stirred at 20° C. for 0.7 h. Rochelle salt solution (equiv) was added and the mixture was stirred for 20 min. The aqueous mixture was extracted with methylene chloride and filtered. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica (10 cm column, methylene chloride/methanol, 6/1-6/1) followed by recrystallization from acetonitrile/ether and methylene chloride/hexane to afford 1.268 g (90%) of 5-(3-hydroxypropyl)-1-methyl-2-ethylimidazole, as a white solid, m.p. 69°-71° C.

후처리

  1. temperatureto warm
  2. stirringstirred at 20° C. for 0.7 h
  3. stirringthe mixture was stirred for 20 min
  4. extractionThe aqueous mixture was extracted with methylene chloride
  5. filtrationfiltered
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica (10 cm column, methylene chloride/methanol, 6/1-6/1)
  9. customfollowed by recrystallization from acetonitrile/ether and methylene chloride/hexane

출처 및 근거

ORD 기록
ord-7504461b060a4f24905c5fc0b7d08209
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05721261

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