Dimethyl 1-trityl-3,5-pyrazoledicarboxylate → 1-Trityl-3,5-bis(hydroxymethyl)pyrazole

HRID 386348노트

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HRID 386348 반응식
[C:1]([N:20]1[C:24]([C:25](OC)=[O:26])=[CH:23][C:22]([C:29](OC)=[O:30])=[N:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.CCOCC>[C:1]([N:20]1[C:24]([CH2:25][OH:26])=[CH:23][C:22]([CH2:29][OH:30])=[N:21]1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

5

반응물 2

HCID 12377531Dimethyl 1-trityl-3,5-pyrazoledicarboxylateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 123775321-Trityl-3,5-bis(hydroxymethyl)pyrazole수율 90%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

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온도
22.5 °C

실험 절차

To a solution of dimethyl 1-trityl-3,5-pyrazoledicarboxylate (3.200 g, 7.50 mmol) in dry THF (50 mL) were added 30 mL of 1.0 M LiAlH4 in Et2O. The resulting solution was stirred for about 16 h at room temperature (20-25° C.). After this time, the reaction was quenched by the slow addition of 1 mL of distilled water, followed by addition of 1 mL of 10% NaOH and 2.4 mL of water. The solids formed were removed by filtration, and 50 mL of dichloromethane was added to the filtrate. The organic phase was separated, washed with distilled water and a white microcrystalline solid was obtained after evaporation of the solvent under vacuum. Yield: 90% (2.843 g, 6.71 mmol).

후처리

  1. customAfter this time, the reaction was quenched by the slow addition of 1 mL of distilled water
  2. additionfollowed by addition of 1 mL of 10% NaOH and 2.4 mL of water
  3. customThe solids formed
  4. customwere removed by filtration, and 50 mL of dichloromethane
  5. additionwas added to the filtrate
  6. customThe organic phase was separated
  7. washwashed with distilled water
  8. customa white microcrystalline solid was obtained
  9. customafter evaporation of the solvent under vacuum

출처 및 근거

ORD 기록
ord-289c35bd6a904647ac68e4a575b46df0
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372379B2

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