Ethanol → Ethyl 5-(propan-2-yl)-1H-pyrazole-3-carboxylate

HRID 1409976ノート

反応式

HRID 1409976 の反応式
[CH:1]([C:4]1[CH:8]=[C:7]([C:9]([OH:11])=[O:10])[NH:6][N:5]=1)([CH3:3])[CH3:2].[CH2:12](O)[CH3:13].C(Cl)(=O)C>C1C=CC=CC=1>[CH:1]([C:4]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH:6][N:5]=1)([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 702EthanolHCID 6367Acetyl chlorideHCID 178439321HCID 178439321、化合物

生成物 1

HCID 6422484Ethyl 5-(propan-2-yl)-1H-pyrazole-3-carboxylate

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

To a clean round bottom flask equipped with a stir bar, Dean-Stark trap, and reflux condenser was added 3-isopropyl-1H-pyrazole-5-carboxylic acid (1 gram, 6.49 mmol, purchased from Fisher Scientific). 30 mL of ethanol (95%, purchased from Fisher Scientific) was added followed by 30 mL of benzene. 43 μL of acetyl chloride was then added and the solution refluxed over the three days. The solvent was then removed using a Buchi rotoevaporator. The residue was then taken up in ethyl acetate and washed with NaHCO3 (saturated). It was then dried with sodium sulfate, filtered and concentrated. Purification using a Teledyne ISCO silica chromatography (hexanes/ethyl acetate gradient) afforded the desired ester. Yield, 85% 1H-NMR δ 6.7 (s, 1H), 5.1 (bs, NH), 4.41 (q, 2H), 3.13 (septet, 1H), 1.38 (t, 3H), 1.33 (d, 6H).

後処理

  1. customTo a clean round bottom flask equipped with a stir bar
  2. temperatureDean-Stark trap, and reflux condenser
  3. temperaturethe solution refluxed over the three days
  4. customThe solvent was then removed
  5. washwashed with NaHCO3 (saturated)
  6. dry with materialIt was then dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification

出典と根拠

ORDレコード
ord-a9e3967f4f1849dc8f7d1697f7cbdf3d
出典データセット
uspto-grants-2014_12
特許番号
US08921401B2

反応ノート

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