Sodium hydride → HCID 54350758, 화합물

HRID 1432882노트

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HRID 1432882 반응식
[H-].[Na+].[CH3:3][N:4]([CH:6]([P:15](=[O:22])([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])P(=O)(OCC)OCC)[CH3:5].[Cl:23][C:24]1[S:28][C:27]([CH:29]=O)=[CH:26][CH:25]=1>C1COCC1>[CH2:20]([O:19][P:15]([C:6]([N:4]([CH3:3])[CH3:5])=[CH:29][C:27]1[S:28][C:24]([Cl:23])=[CH:25][CH:26]=1)(=[O:22])[O:16][CH2:17][CH3:18])[CH3:21]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 817002-Thiophenecarboxaldehyde, 5-chloro-HCID 86795Tetraethyl [(dimethylamino)methylene]bisphosphonate

생성물 1

HCID 54350758HCID 54350758, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a suspension of sodium hydride (0.25 g, 6.25 mmol, 60% mineral oil dispersion) in 10 mL of THF is added slowly a solution of tetraethyl dimethylaminomethylenediphosphonate (2.03 g, 6.14 mmol, prepared according to the procedure described in Psaume, Montury, and Cosmetic Comm. 1982, 12, 415) in 10 mL of THF. After stirring 1 h, a solution of 5-chloro-2-thiophene carboxaldehyde (0.90 g, 6.14 mmol) in 10 mL of THF is added. The resulting mixture is heated at reflux for 1 h, then cooled to room temperature. The reaction mixture is partitioned between Et2O and water. The organic layer is washed sequentially with 1N HCl, water and saturated NaCl, then dried over MgSO4, filtered and concentrated. The crude product is purified via flash column chromatography eluting with a gradient of 40% EtOAc/hexanes to 50% EtOAc/hexanes to afford the title compound (1.52 g, 4.69 mmol) as an oil. 1H NMR (CDCl3, 300 MHz) δ7.20 (d, 1H), 6.95 (d, 1H), 6.82 (d, 1H), 4.15 (m, 4H), 2.62 (s, 6H), 1.60 (t, 6H).

후처리

  1. customprepared
  2. temperatureThe resulting mixture is heated
  3. temperatureat reflux for 1 h
  4. customThe reaction mixture is partitioned between Et2O and water
  5. washThe organic layer is washed sequentially with 1N HCl, water and saturated NaCl
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product is purified via flash column chromatography
  10. washeluting with a gradient of 40% EtOAc/hexanes to 50% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-54efc10ab05d4df79be50323fc6564b4
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612075B2

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