Formaldehyde → Ethyl 2-cyano-3-hydroxypropanoate

HRID 1910364ノート

反応式

HRID 1910364 の反応式
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]

参加物

6

反応物 3

HCID 712FormaldehydeHCID 7764Ethyl cyanoacetateHCID 11776Triphenylphosphine

生成物 1

HCID 11008022Ethyl 2-cyano-3-hydroxypropanoate収率 64%

試薬・触媒・溶媒 2

HCID 5377512Rhodium, dicarbonyl(2,4-pentanedionato)-触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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))

出典と根拠

ORDレコード
ord-f4155ef1c33b461eb3f7e3db2ada1976
出典データセット
uspto-grants-2013_12
特許番号
US08603726B2

反応ノート

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