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

HRID 1948257ノート

反応式

HRID 1948257 の反応式
[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

参加物

4

反応物 2

HCID 866149681-(4-Chlorobenzyl)-6-oxo-1,6-dihydropyridine-3-carbaldehydeHCID 178490219HCID 178490219、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6bf9695163f54cbeb41029f82402e9e6
出典データセット
uspto-grants-2013_03
特許番号
US08399493B2

反応ノート

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