2-(3-Oxo-5-phenyl-trans-1-pentenyl)-3-(5-carboethoxypentyloxy)-4-pyrone → 2-[(3RS)-3-hydroxy-5-phenyl-trans-1-pentenyl]-3-(5-carboethoxypentyloxy)-4-pyrone

HRID 1856402

Reaktionsgleichung

Reaktionsgleichung von HRID 1856402
[O:1]=[C:2]([CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)/[CH:3]=[CH:4]/[C:5]1[O:6][CH:7]=[CH:8][C:9](=[O:22])[C:10]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C([BH-](CC)CC)C.[Li+]>O1CCCC1>[OH:1][CH:2]([CH2:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)/[CH:3]=[CH:4]/[C:5]1[O:6][CH:7]=[CH:8][C:9](=[O:22])[C:10]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]

Komponenten

4

Edukt 2

HCID 233448642-(3-Oxo-5-phenyl-trans-1-pentenyl)-3-(5-carboethoxypentyloxy)-4-pyroneHCID 23664628Lithiumtriethylborohydride

Produkt 1

HCID 233448652-[(3RS)-3-hydroxy-5-phenyl-trans-1-pentenyl]-3-(5-carboethoxypentyloxy)-4-pyroneAusbeute 28,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution, cooled under nitrogen to -78°, of 0.823 g (1.99 mmol) of 2-(3-oxo-5-phenyl-trans-1-pentenyl)-3-(5-carboethoxypentyloxy)-4-pyrone in 4 ml of tetrahydrofuran was added dropwise keeping the internal temperature at -70° to -75°, 1.89 ml (1.89 mmole) of lithium triethylborohydride. After being stirred for an additional 30 min the cold reaction was quenched by the addition of 2.0 ml of 40% aqueous acetic acid and then partially concentrated under reduced pressure. The residue was dissolved in methylene chloride and washed successively with aqueous sodium bicarbonate and brine solution. The organic solution was dried over magnesium sulfate and evaporated to give an oil. Chromatographic purification on silica gel eluting with ether furnished 0.233 g (28%) of 2-[(3RS)-3-hydroxy-5-phenyl-trans-1-pentenyl]-3-(5-carboethoxypentyloxy)-4-pyrone. NMR (CDCl3, 100 M Hz): δ1.26 (3H, t, J=7.0 Hz), 2.32 (2H, t, J=6 Hz).

Aufarbeitung

  1. additionwas added dropwise
  2. customat -70° to -75°
  3. customthe cold reaction
  4. customwas quenched by the addition of 2.0 ml of 40% aqueous acetic acid
  5. concentrationpartially concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in methylene chloride
  7. washwashed successively with aqueous sodium bicarbonate and brine solution
  8. dry with materialThe organic solution was dried over magnesium sulfate
  9. customevaporated
  10. customto give an oil
  11. customChromatographic purification on silica gel eluting with ether

Quellen und Nachweise

ORD-Eintrag
ord-bc53923db60e4c3fac044b9a9a913374
Quelldatensatz
uspto-grants-1980_08
Patentnummer
US04219483

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