2,6-Lutidine → HCID 66728774、化合物

HRID 1098585ノート

反応式

HRID 1098585 の反応式
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])[C:2]([CH3:4])=[O:3].N1C(C)=CC=CC=1C.[CH3:17][C:18]([CH3:22])([CH3:21])[C:19]#[N:20]>>[C:18]([C:19]1[O:3][C:2]([C:1]([O:6][CH2:7][CH3:8])=[O:5])=[CH:4][N:20]=1)([CH3:22])([CH3:21])[CH3:17]

参加物

4

反応物 3

HCID 79372,6-LutidineHCID 12041Ethyl pyruvateHCID 12416Pivalonitrile

生成物 1

HCID 66728774HCID 66728774、化合物収率 29%

実験手順

A solution of ethyl pyruvate (2.0 g, 17.2 mmol) and HDNIB (9.7 g, 20.7 mmol) in trimethylacetonitrile (15 mL) was heated to reflux for 3 hours. After the reaction mixture was cooled to RT, 2,6-lutidine (0.2 mL, 1.7 mmol) was added. The reaction mixture was refluxed for an additional 8 hours. The reaction was checked by LC-MS and the solvent was removed. The residue was dissolved in CH2Cl2C washed with water and brine, dried (Na2SO4), concentrated in vacuo and purified via silica gel column chromatography (EtOAc/hexane) to obtain ethyl 2-tert-butyloxazole-5-carboxylate (1.0 g, 29% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.89 (s, 1H), 4.42 (d, J=7.2 Hz, 2H), 1.49 (s, 9H), 1.43 (d, J=7.2 Hz, 3H); MS (ESI) m/z: 198.1 (M+H+).

後処理

  1. temperatureto reflux for 3 hours
  2. temperatureThe reaction mixture was refluxed for an additional 8 hours
  3. customthe solvent was removed
  4. dissolutionThe residue was dissolved in CH2Cl2C
  5. washwashed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. custompurified via silica gel column chromatography (EtOAc/hexane)

出典と根拠

ORDレコード
ord-6740de7426e64ae0a226b8380a399d4e
出典データセット
uspto-grants-2012_03
特許番号
US08143293B2

反応ノート

読み込み中…