Tetrahydrofuran → HCID 178448063, compound

HRID 1646470Notes

Reaction equation

HRID 1646470 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[CH2:12]([C@H:15]1[CH2:20][CH2:19][C@H:18]([C@H:21]2[CH2:26][CH2:25][C@H:24]([CH2:27][C:28](O)=[O:29])[CH2:23][CH2:22]2)[CH2:17][CH2:16]1)[CH2:13][CH3:14].[OH-].[Na+]>O.C(OCC)(=O)C>[OH:29][CH2:28][CH2:27][C@H:24]1[CH2:25][CH2:26][C@H:21]([C@H:18]2[CH2:19][CH2:20][C@H:15]([CH2:12][CH2:13][CH3:14])[CH2:16][CH2:17]2)[CH2:22][CH2:23]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 178448064HCID 178448064, compound

Product 1

HCID 178448063HCID 178448063, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Into a three-necked flask having a 500 ml capacity was added lithium aluminum hydride (2.8 g), and cooled down to 0° C., followed by dropwise adding tetrahydrofuran (50 ml) and a solution of trans-4-(trans-4-n-propylcyclohexyl)cyclohexyl-acetic acid (26.6 g, 0.1 mol) in this order, agitating the mixture at room temperature for 4 hours to obtain a mixture. To this mixture ethyl acetate (10 ml), water (10 ml) and 2N NaOH aqueous solution (10 ml) were added in this order and refluxed for 30 minutes, followed by cooling the resulting material, filtering, concentrating the filtrate under reduced pressure, adding water (100 ml) and toluene (100 ml), removing the resulting aqueous layer, washing the resulting organic layer with water till the washing water became neutral, drying over anhydrous sodium sulfate, removing a drying agent, concentrating under reduced pressure, passing the residue through an alumina column using dichloromethane solvent, distilling off dichloromethane, recrystallizing from heptane and drying to obtain the captioned compound (21.5 g). Its structure was confirmed by NMR spectra.

Workup

  1. customInto a three-necked flask having
  2. customto obtain a mixture
  3. temperaturerefluxed for 30 minutes
  4. temperatureby cooling the resulting material
  5. filtrationfiltering
  6. concentrationconcentrating the filtrate under reduced pressure
  7. additionadding water (100 ml) and toluene (100 ml)
  8. customremoving the resulting aqueous layer
  9. washwashing the resulting organic layer with water till the washing water
  10. dry with materialdrying over anhydrous sodium sulfate
  11. customremoving a drying agent
  12. concentrationconcentrating under reduced pressure
  13. distillationdistilling off dichloromethane
  14. customrecrystallizing from heptane
  15. customdrying

Sources & evidence

ORD record
ord-b2427027918e4ba1bb5d586477cc07b8
Source dataset
uspto-grants-1993_01
Patent number
US05180519

Reaction notes

Loading…