Chloroform → 4-(3-Methoxyphenyl)-1,3-dimethylpyridin-2(1H)-one

HRID 1903358

反応式

HRID 1903358 の反応式
COC(C[C:6]1([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[CH2:11][CH2:10][N:9]([CH3:12])[C:8](=[O:13])[C:7]1=[CH2:14])=O.[OH-].[K+].CO.O.C(Cl)(Cl)Cl>CO.O>[CH3:12][N:9]1[CH:10]=[CH:11][C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[C:7]([CH3:14])[C:8]1=[O:13]

参加物

7

反応物 4

HCID 6212ChloroformHCID 14797Potassium HydroxideHCID 129475534-Methoxycarbonylmethyl-4-(3'-methoxyphenyl)-1-methyl-3-methylene-2-piperidoneHCID 22242641Methanol--water (1/1)

生成物 1

HCID 204685844-(3-Methoxyphenyl)-1,3-dimethylpyridin-2(1H)-one収率 20%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

4-Carboxymethyl-4-(3'-methoxyphenyl-1-methyl-3-methylene-2-piperidone (29). To methyl ester 28 of Example 10 (1.20 g, 3.97 mmol) dissolved in CH3OH (5 mL, 0° C.) was rapidly added KOH (775 mg, 11.9 mmol) in 5 mL of 1/1 CH3OH/H2O. After 20 h at 25° C., CHCl3 (20 mL) and H2O (20 mL) were added, the separated aqueous layer was extracted with CHCl3 (20 mL) and the combined organic phases were dried and evaporated to give 178 mg (20%) of 1,3-dimethyl-4-(3'-methoxyphenyl)-2-pyridone (this arises from unreacted allylic alcohol under the alkaline hydrolysis conditions): NMR δ7.20 (m, 2H), 6.86 (m, 3H), 6.07 (d,J=7 Hz, 1H), 3.81 (s, 3H), 3.57 (s, 3H), 2.10 (s, 3H): IR (neat) 1640 cm-1 (broad); mass spectrum m/e (rel intensity) 229 (63), 228 (100). Anal. Calcd for C14H15NO2 : C, 73.3; H, 6.6; N, 6.1. Found: C, 73.0; H, 6.6; N, 6.1.

後処理

  1. extractionthe separated aqueous layer was extracted with CHCl3 (20 mL)
  2. customthe combined organic phases were dried
  3. customevaporated

出典と根拠

ORDレコード
ord-8a51106499f04e5dadb3d4137b76d666
出典データセット
uspto-grants-1984_03
特許番号
US04435572

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