HCID 20191518, compound → HCID 20191515, compound

HRID 2118937Notes

Reaction equation

HRID 2118937 reaction equation
[C:1]([C:6]1[CH2:7][CH:8]([CH:16]=[CH2:17])[O:9][C:10]=1[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])([O:3][CH2:4][CH3:5])=[O:2]>C(OCC)(=O)C>[C:1]([C:6]1[CH2:7][CH:8]([CH2:16][CH3:17])[O:9][C:10]=1[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])([O:3][CH2:4][CH3:5])=[O:2]

Participants

3

Reactant 1

HCID 20191518HCID 20191518, compound

Product 1

HCID 20191515HCID 20191515, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Carbethoxy-5-pentyl-2-vinyl-2,3-dihydrofuran prepared in accordance with the procedure of Example I was hydrogenated to obtain 4-carbethoxy-2-ethyl-5-pentyl-2,3-dihydrofuran. For the reaction, 13 grams of the 4-carbethoxy-5-pentyl-2-vinyl-2,3-dihydrofuran and 75 mls ethyl acetate were charged to the reactor of a Parr apparatus. The system was thoroughly purged with nitrogen and 0.65 gram of a hydrogenation catalyst (5 percent palladium on carbon) was added under a nitrogen atmosphere. After additional nitrogen purging, shaking was begun and the system was pressurized with hydrogen to 15 psig. The system was repressurized as necesary until no futher hydrogen uptake was noted. The reaction mixture was then filtered through Dicalite® to remove the catalyst. Ethyl acetate was removed under reduced pressure. Gas chromatographic analysis indicated 98 percent yield crude 4-carbethoxy-2-ethyl-5-pentyl-2,3-dihydrofuran. The crude product was fractionated using a spinning-band distillation apparatus to obtain essentially pure 4-carbethoxy-2-ethyl-5-pentyl-2,3-dihydrofuran (B.P. 112°-114° C. Ε 1 mm Hg. nD≅° 1.4636). The structure ##STR11## was confirmed by infrared and nuclear magnetic resonance spectroscopy.

Workup

  1. additionwere charged to the reactor of a Parr apparatus
  2. customThe system was thoroughly purged with nitrogen and 0.65 gram of a hydrogenation catalyst (5 percent palladium on carbon)
  3. additionwas added under a nitrogen atmosphere
  4. filtrationThe reaction mixture was then filtered through Dicalite®
  5. customto remove the catalyst
  6. customEthyl acetate was removed under reduced pressure

Sources & evidence

ORD record
ord-fb70eae1aa00465bad74802834761560
Source dataset
uspto-grants-1987_07
Patent number
US04681703

Reaction notes

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