Acetic Acid → 2-(3-Oxo-5-phenyl-trans-1-pentenyl)-3-(5-carboethoxypentyloxy)-4-pyrone

HRID 2163267

반응식

HRID 2163267 반응식
[H-].[Na+].[O:3]=[C:4]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:5]P(=O)(OC)OC.[CH:20]([C:22]1[O:23][CH:24]=[CH:25][C:26](=[O:39])[C:27]=1[O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=O.C(O)(=O)C>C1COCC1>[O:3]=[C:4]([CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)/[CH:5]=[CH:20]/[C:22]1[O:23][CH:24]=[CH:25][C:26](=[O:39])[C:27]=1[O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 2733973Dimethyl(2-oxo-4-phenylbutyl)phosphonateHCID 233448502-Formyl-3-(5-carboethoxypentyloxy)-4-pyrone

생성물 1

HCID 233448642-(3-Oxo-5-phenyl-trans-1-pentenyl)-3-(5-carboethoxypentyloxy)-4-pyrone수율 64%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution, under nitrogen, of 0.187 g (3.9 mmole) of sodium hydride (50% dispersion in mineral oil) in 10 ml of dry THF was added dropwise 1.2 g (4.95 mmole) of dimethyl (2-oxo-4-phenylbutyl)-phosphonate. The heterogeneous mixture was stirred for 1.0 hour then a solution of 1.0 g (3.54 mmole) of 2-formyl-3-(5-carboethoxypentyloxy)-4-pyrone, prepared by the procedure of Examples 1 and 2, in 5 ml of THF was added. The mixture was stirred for 15 min then was neutralized to pH 7 with glacial acetic acid. The neutralized solution was concentrated by rotary evaporation and the residue dissolved in methylene chloride. The organic solution was washed with saturated brine solution and dried over magnesium sulfate. Removal of the solvent left an oil which was purified by chromatography on silica gel using ether as the eluent. Concentration of the fractions containing product furnished 0.90 g (64%) of pure 2-(3-oxo-5-phenyl-trans-1-pentenyl)-3-(5-carboethoxypentyloxy)-4-pyrone, m.p. 38.5-40°. NMR (CDCl3): δ1.26 (3H, t, J = 7 Hz); 2.35 (2H, t, J = 6.5 Hz).

후처리

  1. additionwas added
  2. stirringThe mixture was stirred for 15 min
  3. concentrationThe neutralized solution was concentrated by rotary evaporation
  4. dissolutionthe residue dissolved in methylene chloride
  5. washThe organic solution was washed with saturated brine solution
  6. dry with materialdried over magnesium sulfate
  7. customRemoval of the solvent
  8. waitleft an oil which
  9. customwas purified by chromatography on silica gel
  10. additionConcentration of the fractions containing product

출처 및 근거

ORD 기록
ord-14c81869936b46e58615bfd53f210926
출처 데이터셋
uspto-grants-1979_01
특허 번호
US04132847

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