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

反応式

HRID 1856402 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 233448652-[(3RS)-3-hydroxy-5-phenyl-trans-1-pentenyl]-3-(5-carboethoxypentyloxy)-4-pyrone収率 28.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-bc53923db60e4c3fac044b9a9a913374
出典データセット
uspto-grants-1980_08
特許番号
US04219483

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