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

HRID 1809953Notes

Reaction equation

HRID 1809953 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-975ff42b56904603a448c685dfa19abf
Source dataset
uspto-grants-2013_01
Patent number
US08362003B2

Reaction notes

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