Ethyl Acetate → Ethyl [5-oxooctahydropentalen-2-yl]acetate

HRID 1039972Notes

Reaction equation

HRID 1039972 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]1[CH2:13][CH:12]2[CH:8]([CH2:9][C:10]3(OCC(C)(C)C[O:14]3)[CH2:11]2)[CH2:7]1)[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CCOC(C)=O>CC(C)=O.O>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]1[CH2:13][CH:12]2[CH:8]([CH2:9][C:10](=[O:14])[CH2:11]2)[CH2:7]1)[CH3:2]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 86731803ethyl[5,5-dimethylhexahydro-1'H-spiro[1,3-dioxane-2,2'-pentalen]-5'-yl]acetate

Product 1

HCID 67249634Ethyl [5-oxooctahydropentalen-2-yl]acetateYield 13.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of the product of Step 3 (400 mg, 1.350 mmol) in acetone (8.0 mL) and water (8.00 mL) was stirred at room temperature 16 hrs with p-toluenesulfonic acid monohydrate (257 mg, 1.35 mmol). The volatiles were removed under reduced pressure and the residue was partitioned between EtOAc and brine. The separated organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. Flash chromatography (10 to 60% EtOAc in hexanes) afforded ethyl[5-oxooctahydropentalen-2-yl]acetate (38 mg, 0.181 mmol, 13.4% yield) as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 4.14-4.09 (m, 2H), 2.73-2.71 (m, 2H), 2.53-2.47 (m, 2H), 2.37-2.32 (m, 3H), 2.29-2.25 (m, 2H), 2.08-2.02 (m, 2H), 1.27-1.24 (m, 3H).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue was partitioned between EtOAc and brine
  3. dry with materialThe separated organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-438c22212ed043c185ae48de66296ef5
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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