Ethylene Glycol → (3'aR,6'aS)-hexahydro-1'H-spiro(1,3-dioxolane-2,2'-pentalen)-5'-one

HRID 1025792Notes

Reaction equation

HRID 1025792 reaction equation
[CH2:1]1[C@@H:8]2[C@@H:4]([CH2:5][C:6](=[O:9])[CH2:7]2)[CH2:3][C:2]1=[O:10].[CH2:11](O)[CH2:12][OH:13].CC1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH2:1]1[C@H:8]2[C@H:4]([CH2:5][C:6](=[O:9])[CH2:7]2)[CH2:3][C:2]21[O:13][CH2:12][CH2:11][O:10]2

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 178516323HCID 178516323, compound

Product 1

HCID 11030443(3'aR,6'aS)-hexahydro-1'H-spiro(1,3-dioxolane-2,2'-pentalen)-5'-oneYield 31%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

cis-Tetrahydropentalene-2,5(1H,3H)-dione (5 g, 36 mmol) and ethylene glycol (2.3 g, 36 mmol) were dissolved in toluene. To the resulting solution was added PTSA (684 mg, 3.6 mmol). The reaction mixture was refluxed for 12 h meanwhile the resulting water was removed away. Direct chromatography on silica gel gave 2.0 g (11 mmol, yield: 31%) of the desired product, (3a′R,6a′S)-tetrahydro-1′H-spiro[1,3-dioxolane-2,2′-pentalen]-5′(3H)-one: MS (m/e): 183 (M+1)+.

Workup

  1. customwas removed away

Sources & evidence

ORD record
ord-423e38617a06487db67ba4164d258fb7
Source dataset
uspto-grants-2014_05
Patent number
US08729063B2

Reaction notes

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