Formaldehyde → HCID 118308759, compound

HRID 923478Notes

Reaction equation

HRID 923478 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[N:6][CH:7]=1.CN([CH:16]=[O:17])C.[CH2:18]=[O:19].C[O-].[Na+]>C(O)(=O)C>[OH:19][CH2:18][C:8]([CH2:16][OH:17])([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6228DimethylformamideHCID 10942334Sodium MethoxideHCID 59382640HCID 59382640, compound

Product 1

HCID 118308759HCID 118308759, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 575 mg of methyl (5-methylpyridin-2-yl)acetate and 11.5 ml of DMF were added 314 mg of paraformaldehyde and 38 mg of sodium methoxide under ice-cooling, followed by stirring at room temperature for 24 hours. The reaction mixture was ice-cooled and 50 μl of acetic acid was added thereto, followed by concentrating under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 462 mg of methyl 3-hydroxy-2-(hydroxymethyl)-2-(5-methylpyridin-2-yl)propanoate.

Workup

  1. temperaturecooling
  2. temperaturecooled
  3. concentrationby concentrating under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-167b92e9311e4e9dbad3d54ad9cc096c
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

Loading…