2-Cyclopenten-1-one → HCID 14267878, compound

HRID 2214109Notes

Reaction equation

HRID 2214109 reaction equation
[C:1]1([C@@H:7]([C@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[OH:10])[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20](S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C1(=O)CCC=C1>C1CCCCC1>[C:11]1([C@H:9]2[C@H:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[O:8][C:17]3([CH2:22][CH2:21][CH:20]=[CH:27]3)[O:10]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 135882-Cyclopenten-1-oneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 853020(S,S)-(-)-HYDROBENZOIN

Product 1

HCID 14267878HCID 14267878, compoundYield 676.8%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

A solution of (S,S)-hydrobenzoin (10.0 g, 46.7 mmol), pyridinium p-toluene sulfonate (1.4 g, 5.6 mmol), 2-cyclopentene-1-one (20 mL, 238.7 mmol) and cyclohexane (200 mL) was heated under reflux for 4 h with a Dean-Stark trap to remove water formed during the reaction. The mixture was then cooled in an ice bath for 20 min, and the insolubles were filtered off through filter aid. The resulting solution was washed with a 10% aqueous potassium bicarbonate solution (2×25 mL) and water (2×25 mL), and then dried over anhydrous sodium sulfate. The dried solution was passed through a pad of silica gel 60 (26 g of 230–400 mesh). The pad was further eluted with additional hexanes (475 mL). The resulting solution was concentrated in vacuo to afford 2(S),3(S)-diphenyl-1,4-dioxa-spiro[4.4]non-6-ene (10.55 g, 81%) as a white solid.

Workup

  1. temperatureunder reflux for 4 h with a Dean-Stark trap
  2. customto remove water
  3. customformed during the reaction
  4. temperatureThe mixture was then cooled in an ice bath for 20 min
  5. filtrationthe insolubles were filtered off
  6. filtrationthrough filter aid
  7. washThe resulting solution was washed with a 10% aqueous potassium bicarbonate solution (2×25 mL) and water (2×25 mL)
  8. dry with materialdried over anhydrous sodium sulfate
  9. washThe pad was further eluted with additional hexanes (475 mL)
  10. concentrationThe resulting solution was concentrated in vacuo

Sources & evidence

ORD record
ord-497a02f2e1304c5bb219081ac24d5421
Source dataset
uspto-grants-2006_09
Patent number
US07105671B2

Reaction notes

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