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

HRID 386348ノート

反応式

HRID 386348 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
22.5 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-289c35bd6a904647ac68e4a575b46df0
出典データセット
uspto-grants-2013_02
特許番号
US08372379B2

反応ノート

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