Propionic Acid → 4-Hydroxy-6-methyl-3-propanoyl-2H-pyran-2-one

HRID 2277024Notes

Reaction equation

HRID 2277024 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.[C:25](O)(=[O:28])[CH2:26][CH3:27]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[C:25](=[O:28])[CH2:26][CH3:27]

Participants

6

Reactant 3

HCID 1032Propionic AcidHCID 10868DicyclohexylcarbodiimideHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 546842724-Hydroxy-6-methyl-3-propanoyl-2H-pyran-2-one

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To 4-hydroxy-6-methyl-2H-pyran-2-one (18 g; 143 mmol; Aldrich) in 300 ml DCM at 0° C., was added TEA (20 ml; 143 mmol; Aldrich), DCC (30 g; 145 mmol; Aldrich), DMAP (5.25 g; 42.7 mmol; Aldrich) and propionic acid (11 ml; 147 mmol; Aldrich). The reaction mixture was stirred at 0° C. for 1 h, stirred at 25° C. for 18 h, and filtered via vacuum filtration. The filtrate was washed with 5% HCl, dried with brine and anhydrous Na2SO4, and evaporated to a white solid.

Workup

  1. stirringstirred at 25° C. for 18 h
  2. filtrationfiltered via vacuum filtration
  3. washThe filtrate was washed with 5% HCl
  4. dry with materialdried with brine and anhydrous Na2SO4
  5. customevaporated to a white solid

Sources & evidence

ORD record
ord-b104cc87cde049c7a8aa209a042c83f0
Source dataset
uspto-grants-2015_09
Patent number
US09133155B2

Reaction notes

Loading…