Acetic Acid → 2-(3-Oxo-trans-1-octenyl)-3-(5-carboethoxypentyloxy)-6-(trimethylacetoxymethyl)-4-pyrone

HRID 1856399ノート

反応式

HRID 1856399 の反応式
[H-].[Na+].[O:3]=[C:4]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:5]P(=O)(OC)OC.[CH:17]([C:19]1[O:20][C:21]([CH2:37][O:38][C:39](=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41])=[CH:22][C:23](=[O:36])[C:24]=1[O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=O.C(O)(=O)C>C1COCC1>[O:3]=[C:4]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])/[CH:5]=[CH:17]/[C:19]1[O:20][C:21]([CH2:37][O:38][C:39](=[O:44])[C:40]([CH3:41])([CH3:42])[CH3:43])=[CH:22][C:23](=[O:36])[C:24]=1[O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 580181Dimethyl (2-oxoheptyl)phosphonateHCID 233448512-Formyl-3-(5-carboethoxypentyloxy)-6-(trimethylacetoxymethyl)-4-pyrone

生成物 1

HCID 233448542-(3-Oxo-trans-1-octenyl)-3-(5-carboethoxypentyloxy)-6-(trimethylacetoxymethyl)-4-pyrone収率 22.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution, under nitrogen, of 0.206 g (4.3 mmole) of sodium hydride (50% dispersion in mineral oil) in 15 ml of dry THF was added dropwise 1.04 g (4.69 mmole) of dimethyl (2-oxoheptyl)-phosphonate. The heterogeneous mixture was stirred for 1.0 hour then a solution of 1.55 g (3.9 mmole) of 2-formyl-3-(5-carboethoxypentyloxy)-6-(trimethylacetoxymethyl)-4-pyrone 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 0.425 g (22%) of pure 2-(3-oxo-trans-1-octenyl)-3-(5-carboethoxypentyloxy)-6-(trimethylacetoxymethyl)-4-pyrone as an oil. NMR (CDCl3): δ0.88 (3H, t, J=5 Hz); 1.25 (9H, s), 2.27 (2H, t, J=6.5 Hz); 2.60 (2H, t, J=6.5 Hz); 4.91 (2H, s).

後処理

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

出典と根拠

ORDレコード
ord-f0c839046086411f8992ee28fb63ded5
出典データセット
uspto-grants-1980_08
特許番号
US04219483

反応ノート

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