Formaldehyde → Ethyl 2-cyano-3-hydroxypropanoate

HRID 1910364Notes

Reaction equation

HRID 1910364 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]=[O:21].[C:22]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])#[N:23]>C/C(/O)=C/C(C)=O.[C-]#[O+].[C-]#[O+].[Rh].O1CCCC1>[C:22]([CH:24]([CH2:20][OH:21])[C:25]([O:27][CH2:28][CH3:29])=[O:26])#[N:23]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 7764Ethyl cyanoacetateHCID 11776Triphenylphosphine

Product 1

HCID 11008022Ethyl 2-cyano-3-hydroxypropanoateYield 64%

Reagents, catalysts & solvents 2

HCID 5377512Rhodium, dicarbonyl(2,4-pentanedionato)-CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A reactor was charged with 0.26 g (1 mmol) of acetylacetonatodicarbonylrhodium, 0.52 g (2 mmol) of triphenylphosphine, and 200 ml of tetrahydrofuran (THF). The mixture was stirred for 10 minutes in a nitrogen atmosphere. After the dropwise addition of 10.54 g (130 mmol) of a 37% formaldehyde aqueous solution and 11.31 g (100 mmol) of ethyl 2-cyanoacetate, the mixture was reacted at 25° C. for 16 hours with stirring. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate (=10/1)) to obtain 9.16 g of ethyl 2-cyano-3-hydroxypropanoate shown by the following formula (M-18′) (yield: 64%).

Workup

  1. customthe mixture was reacted at 25° C. for 16 hours
  2. stirringwith stirring
  3. customAfter completion of the reaction
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate (=10/1))

Sources & evidence

ORD record
ord-f4155ef1c33b461eb3f7e3db2ada1976
Source dataset
uspto-grants-2013_12
Patent number
US08603726B2

Reaction notes

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