Formaldehyde → Ethyl 2-cyano-3-hydroxypropanoate

HRID 1910364노트

반응식

HRID 1910364 반응식
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]

참가 물질

6

반응물 3

HCID 712FormaldehydeHCID 7764Ethyl cyanoacetateHCID 11776Triphenylphosphine

생성물 1

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

시약·촉매·용매 2

HCID 5377512Rhodium, dicarbonyl(2,4-pentanedionato)-촉매HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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))

출처 및 근거

ORD 기록
ord-f4155ef1c33b461eb3f7e3db2ada1976
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08603726B2

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