2,2-Dimethoxypropane → (3aR,4R,7S,8aR)-Tetrahydro-7-hydroxy-2,2-dimethyl-4,7-methano-1,3-dioxolo[4,5-c]oxepin-6(4H)-one

HRID 1357500Notes

Reaction equation

HRID 1357500 reaction equation
[CH2:1]1[C@@H:6](O)[C@@H:5]([OH:8])[C@H:4]([OH:9])[CH2:3][C@@:2]1([C:11]([OH:13])=[O:12])[OH:10].CO[C:16](OC)([CH3:18])[CH3:17]>CC(C)=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[OH:10][C@@:2]12[CH2:1][C@@H:6]([O:13][C:11]1=[O:12])[C@H:5]1[C@H:4]([O:9][C:16]([CH3:18])([CH3:17])[O:8]1)[CH2:3]2

Participants

5

Reactant 2

HCID 64952,2-DimethoxypropaneHCID 178524980HCID 178524980, compound

Product 1

HCID 10176735(3aR,4R,7S,8aR)-Tetrahydro-7-hydroxy-2,2-dimethyl-4,7-methano-1,3-dioxolo[4,5-c]oxepin-6(4H)-oneYield 86.2%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 180AcetoneSolvent

Procedure

A solution of quinic acid (10.0 g, 52.0 mmol), para-toluenesulfonic acid monohydrate (100 mg, 0.526 mmol) and 2,2-dimethoxypropane (20 mL, 162.9 mmol) in acetone (150 mL) was refluxed for 4 hours. The reaction mixture was concentrated, and the concentrate was dissolved in ethyl acetate (150 mL). The ethyl acetate layer was washed with saturated sodium bicarbonate and brine, dried (MgSO4), filtered and concentrated. The concentrate was stored at 0° C. for several hours to afford 9.6 g (86%) of the desired product as white crystals.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe concentrate was dissolved in ethyl acetate (150 mL)
  3. washThe ethyl acetate layer was washed with saturated sodium bicarbonate and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. waitThe concentrate was stored at 0° C. for several hours

Sources & evidence

ORD record
ord-24a37de267d94e928c214f2beb955342
Source dataset
uspto-grants-2003_07
Patent number
US06593314B1

Reaction notes

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