Sodium Chloride → HCID 44158860, compound

HRID 1952284Notes

Reaction equation

HRID 1952284 reaction equation
[C:1]([O:4][CH2:5][C@@H:6]1[CH2:11][C@@H:10]([OH:12])[CH2:9][CH:8]([OH:13])[O:7]1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Ba+2].BrBr.[Na+].[Cl-]>O>[C:1]([O:4][CH2:5][C@@H:6]1[CH2:11][C@@H:10]([OH:12])[CH2:9][C:8](=[O:13])[O:7]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 10563Barium CarbonateHCID 24408BromineHCID 44158859HCID 44158859, compound

Product 1

HCID 44158860HCID 44158860, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The solution of ((2S,4R)-4,6-dihydroxytetrahydro-2H-pyran-2-yl)methyl acetate (IV) (1 eq) in water was cooled down to 0° C. Barium carbonate (1.4 eq) was added followed by a dropwise addition of Br2 (1.2 eq) and the reaction was stirred overnight at room temperature. The solution was saturated with NaCl and extracted four times with EtOAc. The combined organic phases were dried over MgSO4 and concentrated. The purification using flash chromatography (hexane/acetone=75/25 to 55/45) furnished ((2S,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)methyl acetate (V).

Workup

  1. extractionextracted four times with EtOAc
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. concentrationconcentrated
  4. customThe purification

Sources & evidence

ORD record
ord-26528799eba243da9f8306dbbc35d86f
Source dataset
uspto-grants-2013_03
Patent number
US08404870B2

Reaction notes

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