Ammonium Chloride → CID 275522

HRID 62389

反応式

HRID 62389 の反応式
[O:1]=[C:2]([CH2:8][C:9](=[O:11])[CH3:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(OCC)(OCC)O[CH2:14][CH3:15].[Cl-].[NH4+]>C(O)C>[CH2:14]([O:11][C:9]([CH3:10])=[CH:8][C:2](=[O:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:15]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 31214Ethyl orthoformateHCID 69208Ethyl 2,4-dioxovalerate

生成物 1

HCID 275522CID 275522収率 79%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a stirred solution of ethyl 2,4-dioxopentanoate (36.5 g, 231 mmol) and triethyl orthoformate (41 mL, 246 mmol) in ethanol (60 mL) was added ammonium chloride (3.7 g, 69 mmol). The suspension was stirred at RT overnight. LCMS showed that the reaction was mostly complete. (Hydrolyzes on LCMS to some degree?) The reaction was concentrated under vacuum. The remaining oil was taken up in Et2O (300 mL), filtered to remove insolubles, rinsed with Et2O, and concentrated under vacuum. The product was obtained by short path distillation under vacuum (bp 70 to 77° C. at 0.09 mmHg) to give the product ethyl 4-ethoxy-2-oxopent-3-enoate (36.5 g, 47.3 mmol, 79% yield) as a light yellow oil.

後処理

  1. concentration) The reaction was concentrated under vacuum
  2. filtrationfiltered
  3. customto remove insolubles
  4. washrinsed with Et2O
  5. concentrationconcentrated under vacuum
  6. customThe product was obtained by short path distillation under vacuum (bp 70 to 77° C. at 0.09 mmHg)

出典と根拠

ORDレコード
ord-eeb4172da1ee4a41bf96dbfbbdd0ffdc
出典データセット
uspto-grants-2016_09
特許番号
US09446041B2

関連ノート

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