Water → HCID 19860902, compound

HRID 1165753Notes

Reaction equation

HRID 1165753 reaction equation
[OH:1][C:2]1[CH2:7][CH:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[O:5][C:4](=[O:17])[CH:3]=1.C1CCN2C(=NCCC2)CC1.[C:29](Cl)(=[O:31])[CH3:30].O>C1(C)C=CC=CC=1>[C:29]([O:1][C:2]1[CH2:7][CH:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[O:5][C:4](=[O:17])[CH:3]=1)(=[O:31])[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 70363013HCID 70363013, compound

Product 1

HCID 19860902HCID 19860902, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4.5 g (0.019 mole) of 4-hydroxy-5,6-dihydro-6-nonyl-2-pyrone and 3.15 g (0.021 mole) of DBU in 60 ml of toluene was added dropwise. Then, 1.65 g (0.021 mole) of acetyl chloride with cooling in an ice-water bath. The mixture was stirred for 2 hours and water was added to the reaction mixture. The reaction mixture was extracted with toluene and the toluene layer was washed with an aqueous 5% Na2CO3 solution, with 2N-HCl and finally with an aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed under a reduced pressure to obtain 4.7 g (yield: 89%) of 4-acetoxy-5,6-dihydro-6-nonyl-2-pyrone. The acyloxypyrone was dissolved in 30 ml of toluene and 0.13 g of 4-pyrrolidinopyridine was added to the solution. The mixture was refluxed for 3 hours. The residue obtained by evaporation of the solvent was purified by silica gel column chromatography and recrystallized to obtain 2.4 g (yield: 51%) of 3-acetyl-6-nonyltetrahydropyran-2,4-dione.

Workup

  1. extractionThe reaction mixture was extracted with toluene
  2. washthe toluene layer was washed with an aqueous 5% Na2CO3 solution, with 2N-HCl and finally with an aqueous saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under a reduced pressure

Sources & evidence

ORD record
ord-32bab2b0903d4832ac43572a91dba55b
Source dataset
uspto-grants-1990_03
Patent number
US04912100

Reaction notes

Loading…