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Pyridine → Tert-butyl 4-cyano-3,3-dimethylbutanoate

HRID 585572
ノート
印刷プレビュー

反応式

HRID 585572 の反応式
[NH2:1][C:2](=O)[CH2:3][C:4]([CH3:14])([CH3:13])[CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(OCC)(=O)C>O1CCOCC1>[C:2]([CH2:3][C:4]([CH3:14])([CH3:13])[CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])#[N:1]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 9845Trifluoroacetic anhydrideHCID 21927924Tert-butyl 5-amino-3,3-dimethyl-5-oxopentanoate

生成物 1

HCID 21927900Tert-butyl 4-cyano-3,3-dimethylbutanoate収率 72.4%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane
溶媒

反応条件

温度
0 °C

実験手順

Tert-butyl 5-amino-3,3-dimethyl-5-oxopentanoate (3.17 g, 14.7 mmol) was dissolved in dioxane (32 mL) containing pyridine (8 mL) and the solution was cooled to 0° C. Trifluoroacetic anhydride was added dropwise over 25 minutes keeping the temperature between 0-5° C. The mixture was stirred at 0° C. for one hour and then at room temperature overnight. A few chips of ice were added, followed by ethyl acetate (250 mL). The ethyl acetate was washed with brine, dried (Na2SO4) and removed under reduced pressure. The residue was purified by flash chromatography 7:3 (hexane:ethyl acetate) to give 2.1 g (72%) of the desired product. 1H NMR (CDCl3) 2.44 (s, 2H), 2.21 (s, 2H), 1.39 (s, 9H), 1.10 (s, 6H).

後処理

  1. custombetween 0-5° C
  2. customat room temperature
  3. customovernight
  4. additionA few chips of ice were added
  5. washThe ethyl acetate was washed with brine
  6. dry with materialdried (Na2SO4)
  7. customremoved under reduced pressure
  8. customThe residue was purified by flash chromatography 7:3 (hexane:ethyl acetate)

出典と根拠

ORDレコード
ord-4b7fe4f5df1945b7913a9cf924dacf25
出典データセット
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06933304B2

反応ノート

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