HCID 23344867, compound → HCID 23344866, compound

HRID 1856405Notes

Reaction equation

HRID 1856405 reaction equation
[O:1]=[C:2]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])/[CH:3]=[CH:4]/[C:5]1[O:6][C:7]([CH3:23])=[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]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])/[CH:3]=[CH:4]/[C:5]1[O:6][C:7]([CH3:23])=[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]

Participants

4

Reactant 2

HCID 23344867HCID 23344867, compoundHCID 23664628Lithiumtriethylborohydride

Product 1

HCID 23344866HCID 23344866, compoundYield 27.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution, cooled under nitrogen to -78°, of 1.8 g (4.6 mmol) of 2-(3-oxo-trans-1-octenyl)-6-methyl-3-(5-carboethoxypentyloxy)-4-pyrone in 20 ml of tetrahydrofuran was added dropwise keeping the internal temperature at -70° to -75°, 30 ml (4.6 mmole) of lithium triethylborohydride. After being stirred for an additional 30 min the cold reaction was quenched by the addition of 3.0 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 0.5 g (26%) of 2-[(3RS)-3-hydroxy-trans-1-octenyl]-6-methyl-3-(5-carboethoxypentyloxy)-4-pyrone. NMR (CDCl3, 100 M Hz): δ0.90 (3H, t, J=4.5 Hz), 2.33 (3H, s).

Workup

  1. additionwas added dropwise
  2. customat -70° to -75°
  3. customthe cold reaction
  4. customwas quenched by the addition of 3.0 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

Sources & evidence

ORD record
ord-2ce3b39c9cfa4cd2af1244c49a88d3aa
Source dataset
uspto-grants-1980_08
Patent number
US04219483

Reaction notes

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