Sulfuric Acid → HCID 90019020, compound

HRID 1506959Notes

Reaction equation

HRID 1506959 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C@@H:4]([OH:14])[C@@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13])[OH:6].S(=O)(=O)(O)O>CCC(=O)CC>[CH3:1][O:2][C:3]([C@@H:4]1[C@@H:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[O:6][C:5]([CH2:7][CH3:8])([CH2:4][CH3:3])[O:14]1)=[O:15]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 90018036HCID 90018036, compound

Product 1

HCID 90019020HCID 90019020, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 7288Ethyl ketoneSolvent

Procedure

3-pentanone was added to (2S,3R)-methyl-3-(2-chlorophenyl)-2,3-dihydroxypropanoate at room temperature. Sulfuric acid (H2SO4) was added and stirred at room temperature. The reaction mixture was quenched with H2O, extracted with EA, washed with H2O, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated. The crude compound was purified by a silica gel column to produce the title compound (1.6 g, 60˜85%).

Workup

  1. customThe reaction mixture was quenched with H2O
  2. extractionextracted with EA
  3. washwashed with H2O
  4. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude compound was purified by a silica gel column

Sources & evidence

ORD record
ord-f2ff4000c6bf4e0697e521101ccfb928
Source dataset
uspto-grants-2015_12
Patent number
US09221783B2

Reaction notes

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