Furan → HCID 178520601, compound

HRID 374203Notes

Reaction equation

HRID 374203 reaction equation
C([O:3][C:4](=[S:20])[CH:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)C.F[C:22](F)(F)[C:23]([O:25][C:26](=O)[C:27](F)(F)F)=O.O1C=CC=C1>ClCCl>[O:25]1[CH:26]=[CH:27][CH:22]=[C:23]1[C:11](=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:4]([OH:3])=[S:20]

Participants

5

Reactant 3

HCID 8029FuranHCID 9845Trifluoroacetic anhydrideHCID 53672878HCID 53672878, compound

Product 1

HCID 178520601HCID 178520601, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred, ice-cold solution of 7.75 g. of ethyl-7-carboxy-2-phenylthioheptanoate in 25 ml. of dichloromethane is added 3.5 ml. of trifluoroacetic anhydride during 2 minutes. The solution is stirred at ambient temperature for 10 minutes, recooled to 0° C. and treated with 9 ml. of furan during 2 minutes. The resulting solution is stirred at ambient temperature for 18 hours and then partitioned with 1:1 ether-petroleum either and aqueous sodium bicarbonate. The organic phase is washed with water and brine, dried and evaporated. The resulting crude ester (6.75 g.) is dissolved in 75 ml. of ethanol containing 4.95 g. of 85% potassium hydroxide and 10 ml. of water. This solution is refluxed for 20 minutes, cooled and concentrated in vacuo. The residue is partitioned with water and ether. The aqueous layer is acidified with dilute hydrochloric acid and extracted with ether. This extract is washed with water and brine, dried and evaporated, giving the product as an oil, identified as having a PMRδ 2.80 (2, t, J=7).

Workup

  1. customrecooled to 0° C.
  2. additiontreated with 9 ml
  3. stirringThe resulting solution is stirred at ambient temperature for 18 hours
  4. custompartitioned with 1:1 ether-petroleum either
  5. washThe organic phase is washed with water and brine
  6. customdried
  7. customevaporated
  8. dissolutionThe resulting crude ester (6.75 g.) is dissolved in 75 ml
  9. temperatureThis solution is refluxed for 20 minutes
  10. temperaturecooled
  11. concentrationconcentrated in vacuo
  12. customThe residue is partitioned with water and ether
  13. extractionextracted with ether
  14. washThis extract is washed with water and brine
  15. customdried
  16. customevaporated

Sources & evidence

ORD record
ord-2812285f7e29483da25458085ed0c9b3
Source dataset
uspto-grants-1992_11
Patent number
US05166369

Reaction notes

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