Hydrochloric Acid → HCID 178519222, compound

HRID 516878Notes

Reaction equation

HRID 516878 reaction equation
Cl.[Si]([O:9][C@@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]2[C:17](=[O:27])[O:18][C:19](=[O:26])[C:20]=2[CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)[CH2:12][CH2:11]1)(C(C)(C)C)(C)C>C(O)C>[CH:21]1([C:20]2[C:19](=[O:26])[O:18][C:17](=[O:27])[C:16]=2[C@H:13]2[CH2:14][CH2:15][C@@H:10]([OH:9])[CH2:11][CH2:12]2)[CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178455307HCID 178455307, compound

Product 1

HCID 178519222HCID 178519222, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A catalytic amount of concentrated hydrochloric acid was added to a solution of 3-(cis-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)-4-cyclopentylfuran-2,5-dione (65 mg, 0.17 mmol) in ethanol (3.0 ml) at room temperature, and the mixture was stirred at 50° C. for 5 hr. The reaction mixture was allowed to cool and was then concentrated under reduced pressure. The residue was chromatographed on silica gel column (hexane:ethyl acetate=80:20) to give the title compound as a colorless solid (40 mg, yield 88%).

Workup

  1. temperatureto cool
  2. concentrationwas then concentrated under reduced pressure
  3. customThe residue was chromatographed on silica gel column (hexane:ethyl acetate=80:20)

Sources & evidence

ORD record
ord-e9113966512241e3a69511d200234c50
Source dataset
uspto-grants-2015_08
Patent number
US09115079B2

Reaction notes

Loading…