4-Chloro-3-hydroxybenzaldehyde → Ethyl 6-(4-chloro-3-hydroxyphenyl)-5-(2,6-dimethoxyphenyl)pyridine-2-carboxylate

HRID 1040331노트

반응식

HRID 1040331 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1/[CH:11]=[CH:12]/[CH:13]=[C:14](/[N:20]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)\[C:15]([O:17][CH2:18][CH3:19])=[O:16].[Cl:40][C:41]1[CH:48]=[CH:47][C:44]([CH:45]=O)=[CH:43][C:42]=1[OH:49]>C(#N)C>[Cl:40][C:41]1[CH:48]=[CH:47][C:44]([C:45]2[N:20]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:13]=[CH:12][C:11]=2[C:4]2[C:5]([O:9][CH3:10])=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])=[CH:43][C:42]=1[OH:49]

참가 물질

4

반응물 2

HCID 138651144-Chloro-3-hydroxybenzaldehydeHCID 86637360ethyl (2E,4E)-5-(2,6-dimethoxyphenyl)-2-[(triphenylphosphoranylidene)amino]penta-2,4-dienoate

생성물 1

HCID 66720714Ethyl 6-(4-chloro-3-hydroxyphenyl)-5-(2,6-dimethoxyphenyl)pyridine-2-carboxylate수율 41.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Reflux a solution of 7.54 g (14 mmol) of ethyl (2E,4E)-5-(2,6-dimethoxyphenyl)-2-[(triphenylphosphoranylidene)amino]penta-2,4-dienoate and 2.42 g (15.4 mmol) of 4-chloro-3-hydroxybenzaldehyde in 280 mL of anhydrous acetonitrile for 96 h. After cooling to RT, concentrate the reaction mixture under reduced pressure and purify the residue obtained by silica gel column chromatography, eluting with a cyclohexane/ethyl acetate (EtOAc) gradient from 0 to 30% of EtOAc. After concentration under reduced pressure, we obtain 2.4 g of ethyl 6-(4-chloro-3-hydroxyphenyl)-5-(2,6-dimethoxyphenyl)pyridine-2-carboxylate in the form of white powder.

후처리

  1. concentrationconcentrate the reaction mixture under reduced pressure
  2. custompurify the residue
  3. customobtained by silica gel column chromatography
  4. washeluting with a cyclohexane/ethyl acetate (EtOAc) gradient from 0 to 30% of EtOAc
  5. concentrationAfter concentration under reduced pressure, we

출처 및 근거

ORD 기록
ord-20beb2ca202042fbb269f0de4f2a8f19
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552201B2

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