Sulfuric Acid → HCID 118140937, compound

HRID 1506971Notes

Reaction equation

HRID 1506971 reaction equation
[OH:1][C@H:2]([C@@H:7]([OH:15])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5][CH3:6])=[O:4].[CH3:16][CH2:17][C:18](=O)[CH2:19][CH3:20].OS(O)(=O)=O>CCOC(C)=O>[CH3:6][O:5][C:3]([C@H:2]1[C@H:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:15][C:18]([CH2:19][CH3:20])([CH2:17][CH3:16])[O:1]1)=[O:4]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7288Ethyl ketoneHCID 11063699HCID 11063699, compound

Product 1

HCID 118140937HCID 118140937, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (2R,3S)-methyl 2,3-dihydroxy-4-phenylbutanoate (Preparation example 260, 2.0 g, 9.51 mmol) in 3-pentanone (5 mL, 47.55 mmol) was added a catalytic amount of H2SO4 (0.051 mL, 0.951 mmol) at room temperature. The mixture was stirred for 20 h. The resulting mixture was diluted with EtOAc, washed with water, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude compound was purified by a silica gel column to produce the title compound (1.2 g, 50˜75%)

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude compound was purified by a silica gel column

Sources & evidence

ORD record
ord-d2fc1d814126447d9adcd5aa67d6dfbb
Source dataset
uspto-grants-2015_12
Patent number
US09221783B2

Reaction notes

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