Tetrahydrofuran → HCID 68069072、化合物

HRID 1184440ノート

反応式

HRID 1184440 の反応式
CC([O-:5])(C)C.[K+].[CH3:7][CH:8]1[O:13][C:12]2[CH:14]=[CH:15][C:16]([CH:18]=O)=[CH:17][C:11]=2[NH:10][C:9]1=[O:20].[CH2:21]1[CH2:25][O:24][CH2:23][CH2:22]1>>[CH3:7][CH:8]1[O:13][C:12]2[CH:14]=[CH:15][C:16](/[CH:18]=[CH:22]/[C:23]([O:24][CH2:25][CH3:21])=[O:5])=[CH:17][C:11]=2[NH:10][C:9]1=[O:20]

参加物

4

反応物 3

HCID 8028Tetrahydrofuran2 回HCID 218738872-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehydeHCID 23665647Potassium tert-butoxide

生成物 1

HCID 68069072HCID 68069072、化合物収率 92%

反応条件

温度
0 °C

実験手順

In a 100 mL round bottom flask equipped with a magnetic stir bar was added t-BuOK (352 mg, 3.14 mmol) and THF (5 mL). The solution was cooled to 0° C. Triethylphosphonoacetate (0.576 mL, 2.88 mmol) was added slowly by syringe pump over 30 min. Using 13 (500 mg, 2.62 mmol) in THF (5 mL), the aldehyde was added via syringe pump over 30 min at 0° C. When the addition was complete, the reaction was warmed to room temperature and stirred for 2 h. The reaction was quenched with sat aqueous NH4Cl (10 mL) and extracted with EtOAc. The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash column chromatography using a gradient of 25-50% EtOAc in hexanes. The appropriate fractions were combined and concentrated in vacuo to give the title compound as a white solid (631 mg, 92% yield): 1H NMR (400 MHz, DMSO-d6) δ ppm 1.25 (t, J=7.20 Hz, 3H) 1.43 (d, J=6.82 Hz, 3H) 4.18 (q, J=7.16 Hz, 2H) 4.70-4.77 (m, 1H) 6.38 (d, J=15.92 Hz, 1H) 7.13 (d, J=2.02 Hz, 1H) 7.33 (dd, J=8.72, 2.15 Hz, 1H) 7.56 (d, J=15.92 Hz, 1H) 10.78 (s, 1H). ESI-MS: m/z 262.2 (M+H)+.

後処理

  1. customIn a 100 mL round bottom flask equipped with a magnetic stir bar
  2. additionWhen the addition
  3. temperaturethe reaction was warmed to room temperature
  4. customThe reaction was quenched with sat aqueous NH4Cl (10 mL)
  5. extractionextracted with EtOAc
  6. washThe organic layer was washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-21b17d75868f4748bacc269d4a6cce07
出典データセット
uspto-grants-2014_03
特許番号
US08669249B2

反応ノート

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