Hydrochloric Acid → HCID 58875427, compound

HRID 2377122Notes

Reaction equation

HRID 2377122 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:11])([CH2:9][CH3:10])[CH2:7][CH3:8].C1COCC1.N[C@H]([C:21]([OH:23])=[O:22])C[SeH].[Li]CCCC.Cl>O.C(OCC)(=O)C>[C:21]([C:5]1[O:1][C:2]([C:6]([OH:11])([CH2:9][CH3:10])[CH2:7][CH3:8])=[CH:3][CH:4]=1)([OH:23])=[O:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14810227HCID 14810227, compoundHCID 178511841HCID 178511841, compound

Product 1

HCID 58875427HCID 58875427, compoundYield 71.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

3-(2-Furanyl)pentan-3-ol (3.0 g, 19 mmol) is added to THF (20 mL) under a nitrogen atmosphere. The solution is stirred and cooled to −78° C. Sec-BuLi (1.3 M in cyclohexane, 31 mL, 41 mmol) is added dropwise maintaining the temperature below −55° C. After complete addition, the ice bath is removed and the solution slowly warmed to room temperature where it is stirred for 18 hours. The mixture is cooled to 48° C. and CO2 gas is bubbled through the solution. A thick yellow past results and the temperature is increased to −10° C. Water (50 mL) is added and the solution is stirred at room temperature for 30 minutes. Ethyl acetate is added followed by water and the ph is adjusted to 1 with 1 N HCl. The organic layer is separated and the water layer was discarded. The organic layer is added to 1N NaOH solution and extracted. The pH of the water layer is adjusted to 1 with 1N HCl followed by addition of EtOAc. The organic layer is separated, dried over sodium sulfate, filtered, and evaporated under vacuum to give 2.7 grams of an oil.

Workup

  1. temperaturemaintaining the temperature below −55° C
  2. additionAfter complete addition
  3. customthe ice bath is removed
  4. temperaturethe solution slowly warmed to room temperature where it
  5. stirringis stirred for 18 hours
  6. temperatureThe mixture is cooled to 48° C.
  7. customCO2 gas is bubbled through the solution
  8. customA thick yellow past results
  9. temperaturethe temperature is increased to −10° C
  10. stirringthe solution is stirred at room temperature for 30 minutes
  11. customThe organic layer is separated
  12. additionThe organic layer is added to 1N NaOH solution
  13. extractionextracted
  14. additionfollowed by addition of EtOAc
  15. customThe organic layer is separated
  16. dry with materialdried over sodium sulfate
  17. filtrationfiltered
  18. customevaporated under vacuum

Sources & evidence

ORD record
ord-16efcfa9e02c4c9498a55ff7768e3226
Source dataset
uspto-grants-2008_12
Patent number
US07468449B2

Reaction notes

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