1-(4-Chlorobenzyl)-6-oxo-1,6-dihydropyridine-3-carbaldehyde → 1-(4-chlorobenzyl)-5-(hydroxy(3-methoxyphenyl)methyl)pyridin-2(1H)-one

HRID 1948257노트

반응식

HRID 1948257 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)C[Mg]Br.[Cl:12][C:13]1[CH:28]=[CH:27][C:16]([CH2:17][N:18]2[C:23](=[O:24])[CH:22]=[CH:21][C:20]([CH:25]=[O:26])=[CH:19]2)=[CH:15][CH:14]=1>C1COCC1>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][N:18]2[CH:19]=[C:20]([CH:25]([OH:26])[C:10]3[CH:9]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=3)[CH:21]=[CH:22][C:23]2=[O:24])=[CH:27][CH:28]=1

참가 물질

4

반응물 2

HCID 866149681-(4-Chlorobenzyl)-6-oxo-1,6-dihydropyridine-3-carbaldehydeHCID 178490219HCID 178490219, 화합물

생성물 1

HCID 589669561-(4-chlorobenzyl)-5-(hydroxy(3-methoxyphenyl)methyl)pyridin-2(1H)-one수율 64%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

According to Scheme 7 Method B: A solution of 3-methoxybenzylmagnesium bromide (1.2 eq, 1.00 mmol, 1.00 mL) was added dropwise to a solution of 1-(4-chlorobenzyl)-1,6-dihydro-6-oxopyridine-3-carbaldehyde (1 eq, 1.21 mmol, 0.30 g, Example 10 Step 1) in THF (15 mL) at −78° C. under a nitrogen atmosphere. The reaction mixture was stirred for 14 hours at room temperature. The resulting mixture was poured onto ice and extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered and evaporated. Purification by flash chromatography (AIT Flashsmart prepacked column 25 g SiO2, CH2Cl2/AcOEt 80/20 to 70/30) afford 1-(4-chlorobenzyl)-5-(hydroxy(3-methoxyphenyl)methyl)pyridin-2(1H)-one (0.64 mmol, 0.28 g, 64%) as a yellow semi-solid.

후처리

  1. additionThe resulting mixture was poured onto ice
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography (AIT Flashsmart prepacked column 25 g SiO2, CH2Cl2/AcOEt 80/20 to 70/30)

출처 및 근거

ORD 기록
ord-6bf9695163f54cbeb41029f82402e9e6
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399493B2

반응 노트

불러오는 중…