Potassium Hydroxide → 2-Hydroxymethyl-3-(5-carboethoxypentyloxy)-6-(trimethylacetoxymethyl)-4-pyrone

HRID 2163264Notes

Reaction equation

HRID 2163264 reaction equation
[OH-].[K+].[OH:3][CH2:4][C:5]1[O:6][C:7]([CH2:13][O:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:8][C:9](=[O:12])[C:10]=1[OH:11].I[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>C(O)C.O>[OH:3][CH2:4][C:5]1[O:6][C:7]([CH2:13][O:14][C:15](=[O:20])[C:16]([CH3:17])([CH3:19])[CH3:18])=[CH:8][C:9](=[O:12])[C:10]=1[O:11][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 10880140Ethyl 6-iodohexanoateHCID 233448682-Hydroxymethyl-3-hydroxy-6-(trimethylacetoxymethyl)-4-pyrone

Product 1

HCID 233448562-Hydroxymethyl-3-(5-carboethoxypentyloxy)-6-(trimethylacetoxymethyl)-4-pyroneYield 27%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1.84 g (0.028 mole) of potassium hydroxide in 38 ml of ethanol and 10 ml of water was added 6.76 g (0.026 mole) of 2-hydroxymethyl-3-hydroxy-6-(trimethylacetoxymethyl)-4-pyrone, and the resulting mixture heated to 50°. An 8.3 g (0.03 mole) portion of ethyl 6-iodohexanoate was then added and the resulting clear solution heated at reflux for 7 hr under a nitrogen atmosphere. Removal of the ethanol under reduced pressure left a residue which was dissolved in methylene chloride. The organic solution was washed successively with aqueous NaHCO3 and saturated brine, was dried over magnesium sulfate, and was evaporated to afford a viscous oil. This material was chromatographed on silica gel eluting with ethyl acetate to give 2.9 g (27%) of oily product, 2-hydroxy-3-(5-carboethoxypentyloxy)-6-(trimethylacetoxymethyl)-4-pyrone. NMR (CDCl3): δ1.22 (3H, t, J = 7 Hz), 1.23 (9H, s), 2.30 (2H, t, J = 5.5 Hz), 6.32 (1H, s).

Workup

  1. temperaturethe resulting mixture heated to 50°
  2. temperaturethe resulting clear solution heated
  3. temperatureat reflux for 7 hr under a nitrogen atmosphere
  4. customRemoval of the ethanol under reduced pressure
  5. waitleft a residue which
  6. dissolutionwas dissolved in methylene chloride
  7. washThe organic solution was washed successively with aqueous NaHCO3 and saturated brine
  8. dry with materialwas dried over magnesium sulfate
  9. customwas evaporated
  10. customto afford a viscous oil
  11. customThis material was chromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-5e77b7457b654418a340f01f6629a533
Source dataset
uspto-grants-1979_01
Patent number
US04132847

Reaction notes

Loading…