2,2-Dimethoxypropane → (4R)-4-[(1R)-1-(Benzyloxy)ethyl]-2,2-dimethyl-1,3-dioxolane

HRID 1958960Notes

Reaction equation

HRID 1958960 reaction equation
[CH2:1]([O:8][C@H:9]([CH3:14])[C@H:10]([OH:13])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[C:16]1(C)[CH:21]=CC(S(O)(=O)=O)=C[CH:17]=1.COC(OC)(C)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCOC(C)=O.C(=O)(O)[O-].[Na+]>[CH2:1]([O:8][C@@H:9]([C@H:10]1[CH2:11][O:12][C:16]([CH3:21])([CH3:17])[O:13]1)[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 64952,2-DimethoxypropaneHCID 24436Sodium SulfateHCID 521998p-Toluenesulfonic acid monohydrateHCID 13119193(2R,3R)-3-(Benzyloxy)butane-1,2-diol2×

Product 1

HCID 13119184(4R)-4-[(1R)-1-(Benzyloxy)ethyl]-2,2-dimethyl-1,3-dioxolane

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A stirred solution of (2R,3R)-3-(benzyloxy)butane-1,2-diol (the product of step ii) (0.68 g), p-toluene sulfonic acid monohydrate (34 mg) and 2,2-dimethoxypropane (0.43 mL) in toluene (10 mL) was heated to reflux for 30 min, then anhydrous sodium sulfate was added and reflux continued for 2.5 h. The reaction mixture was allowed to cool and diluted with EtOAc and saturated aqueous sodium bicarbonate and the layers separated. The organic extract was washed with brine, dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography on silica gel using EtOAc/isohexane (1:9 to 1:1 gradient) as eluent to give the subtitle compound as a colourless liquid. Yield: 0.46 g.

Workup

  1. temperatureto reflux for 30 min
  2. temperaturereflux
  3. temperatureto cool
  4. customthe layers separated
  5. extractionThe organic extract
  6. washwas washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e0c389e0c51f4a2db5255c3a8f777be6
Source dataset
uspto-grants-2013_04
Patent number
US08410123B2

Reaction notes

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