Barium Carbonate → (4R,6S)-6-(dimethoxymethyl)-4-hydroxy-tetrahydropyran-2-one

HRID 1261818Notes

Reaction equation

HRID 1261818 reaction equation
[CH3:1][O:2][CH:3]([O:12][CH3:13])[C@H:4]1[O:9][CH:8]([OH:10])[CH2:7][C@H:6]([OH:11])[CH2:5]1.C(=O)([O-])[O-].[Ba+2].BrBr>O>[CH3:1][O:2][CH:3]([O:12][CH3:13])[C@H:4]1[O:9][C:8](=[O:10])[CH2:7][C@H:6]([OH:11])[CH2:5]1

Participants

5

Reactant 3

HCID 10563Barium CarbonateHCID 24408BromineHCID 25050459(4R,6S)-6-(dimethoxymethyl)-tetrahydro-2H-pyran-2,4-diol

Product 1

HCID 67320619(4R,6S)-6-(dimethoxymethyl)-4-hydroxy-tetrahydropyran-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of 1.4 g of (4R,6S)-6-(dimethoxymethyl)-tetrahydro-2H-pyran-2,4-diol (I′) in 100 mL of water, 2.4 g of barium carbonate and 0.5 mL of bromine at 0° C. are added. After 3 hours of stirring at 0-5° C., the product II′ is extracted three times with 300 mL of ethyl acetate. Finally ethyl acetate is distilled off. The residue is flash chromatographed (DIPE/acetonitrile 2/1). The solvents are distilled off to get the title compound.

Workup

  1. extractionthe product II′ is extracted three times with 300 mL of ethyl acetate
  2. distillationFinally ethyl acetate is distilled off
  3. customchromatographed (DIPE/acetonitrile 2/1)
  4. distillationThe solvents are distilled off

Sources & evidence

ORD record
ord-ca10defe221e4410addca8d1efc65d9c
Source dataset
uspto-grants-2013_06
Patent number
US08471045B2

Reaction notes

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