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

HRID 1903358

반응식

HRID 1903358 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-8a51106499f04e5dadb3d4137b76d666
출처 데이터셋
uspto-grants-1984_03
특허 번호
US04435572

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