Triethylamine → 1-[(4-Methoxy)phenyl]-3-(hydroxymethyl)-1H-pyrazole 5-(methoxycarbonyl)pyrazole

HRID 394808ノート

反応式

HRID 394808 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[CH:12][CH:11]=[N:10]2)=[CH:5][CH:4]=1.[CH3:14][O:15][C:16]([C:18]1[NH:22][N:21]=[C:20](C(O)=O)[CH:19]=1)=[O:17].C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+]>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[N:10]2)=[CH:7][CH:8]=1.[CH3:14][O:15][C:16]([C:18]1[NH:22][N:21]=[CH:20][CH:19]=1)=[O:17]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 696917091-[(4-methoxy)phenyl]-1H-pyrazole 5-(methoxycarbonyl)pyrazole-3-carboxylic acid

生成物 1

HCID 696917971-[(4-Methoxy)phenyl]-3-(hydroxymethyl)-1H-pyrazole 5-(methoxycarbonyl)pyrazole収率 97.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-[(4-methoxy)phenyl]-1H-pyrazole-5-(methoxycarbonyl)pyrazole-3-carboxylic acid (2.4 g, 8.69 mmol) in 50 mL of tetrahydrofuran at −20° C. was added triethylamine (1.21 mL, 8.69 mmol) and ethyl chloroformate (0.83 mL, 8.69 mmol). This mixture was stirred for 30 min and then there was added sodium borohydride (0.66 g, 17.4 mmol) in a minimal amount of water. The reaction mixture was stirred with slow warming to room temperature for 1 h and then was quenched with 10% aq HCl. After diluting with ethyl acetate, the organics were washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (elution with 3:2 ethyl acetate/hexane) to afford 1.4 g (61%) of the title compound. LRMS (DCI): 263.3 (M+H)+.

後処理

  1. stirringThe reaction mixture was stirred
  2. customwas quenched with 10% aq HCl
  3. additionAfter diluting with ethyl acetate
  4. washthe organics were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (elution with 3:2 ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-bc20e9de2e284213a852b2318f03ffb5
出典データセット
uspto-grants-2003_08
特許番号
US06602895B2

反応ノート

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