HCID 20191518, compound → HCID 20191515, compound

HRID 462579Notes

Reaction equation

HRID 462579 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-n-pentyl-2-vinyl-2,3-dihydrofuran prepared in accordance with the procedure of Example I was hydrogenated to obtain 4-carbethoxy-5-n-pentyl-2-ethyl-2,3-dihydrofuran. For the reaction, 13 grams 4-carbethoxy-5-n-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) added under a nitrogen atmosphere. After additional nitrogen purging, shaking was begun and the system pressurized with hydrogen to 15 psig. The system was repressurized as necessary until no further hydrogen uptake was noted. The reaction mixture was then filtered through Dicalite® to remove the Pd/carbon catalyst and ethyl acetate removed under reduced pressure. Gas chromatographic analysis indicated 98 percent yield crude 4-carbethoxy-5-n-pentyl-2-ethyl-2,3-dihydrofuran. The crude product was fractionated using a spinning-band distillation apparatus to obtain essentially pure 4-carbethoxy-5-n-pentyl-2-ethyl-2,3-dihydrofuran (B.P. 112°-114° C. @ 1 mm Hg; nD25° 1.4636); which was confirmed by nuclear magnetic resonance and infrared spectroscopic analysis.

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. additionadded under a nitrogen atmosphere
  4. filtrationThe reaction mixture was then filtered through Dicalite®
  5. customto remove the Pd/carbon catalyst and ethyl acetate
  6. customremoved under reduced pressure

Sources & evidence

ORD record
ord-e6793ffda07f4f97961fed476bf3468a
Source dataset
uspto-grants-1985_05
Patent number
US04515978

Reaction notes

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