Hydrochloric Acid → 3a-Methyl-6-(3-oxo-butyl)-1,2,4,5,9a,9b-hexahydro-3aH-9-oxa-cyclopenta[a]naphthalene-3,7-dione

HRID 2358275Notes

Reaction equation

HRID 2358275 reaction equation
Cl.[CH3:2][C:3]12[C:24](=[O:25])[CH2:23][CH2:22][CH:4]1[CH:5]1[C:10]([CH2:11][CH2:12]2)=[C:9]([CH2:13][CH2:14][C:15]2([CH3:20])OCC[O:16]2)[C:8](=[O:21])[CH2:7][O:6]1>CC(C)=O>[CH3:2][C:3]12[C:24](=[O:25])[CH2:23][CH2:22][CH:4]1[CH:5]1[C:10]([CH2:11][CH2:12]2)=[C:9]([CH2:13][CH2:14][C:15](=[O:16])[CH3:20])[C:8](=[O:21])[CH2:7][O:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 684591043a-Methyl-6-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-1,2,4,5,9a,9b-hexahydro-3aH-9-oxa-cyclopenta[a]naphthalene-3,7-dione

Product 1

HCID 684598753a-Methyl-6-(3-oxo-butyl)-1,2,4,5,9a,9b-hexahydro-3aH-9-oxa-cyclopenta[a]naphthalene-3,7-dione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3 N Hydrochloric acid (0.85 mL) was added to a stirred solution of the crude 3a-Methyl-6-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-1,2,4,5,9a,9b-hexahydro-3aH-9-oxa-cyclopenta[a]naphthalene-3,7-dione in acetone (50 mL) at room temperature. The reaction mixture was stirred at room temperature for 0.5 h. The reaction was quenched with saturated sodium bicarbonate aqueous solution (50 mL), and then the acetone was removed under reduced pressure. The residue was diluted with brine (50 mL), extracted with ethyl acetate (2×100 mL), and the combined organic layer was dried with magnesium sulfate. The resulting solution was filtered and the solvent evaporated to yield an oil, which was used in subsequent steps without further purification.

Workup

  1. customThe reaction was quenched with saturated sodium bicarbonate aqueous solution (50 mL)
  2. customthe acetone was removed under reduced pressure
  3. additionThe residue was diluted with brine (50 mL)
  4. extractionextracted with ethyl acetate (2×100 mL)
  5. dry with materialthe combined organic layer was dried with magnesium sulfate
  6. filtrationThe resulting solution was filtered
  7. customthe solvent evaporated
  8. customto yield an oil, which
  9. customwas used in subsequent steps without further purification

Sources & evidence

ORD record
ord-6a217ed4844040039b0fa7fccc495abc
Source dataset
uspto-grants-2010_07
Patent number
US07763648B2

Reaction notes

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