Ammonium Chloride → Acetone O-[5-methoxy-2-(6-methoxy-2-naphthoyl)phenyl]oxime

HRID 1061850노트

반응식

HRID 1061850 반응식
CC(C)([O-])C.[K+].[CH3:7][C:8](=[N:10][OH:11])[CH3:9].F[C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[C:21]([C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[C:28]([O:33][CH3:34])[CH:29]=2)[CH:24]=1)=[O:22].[Cl-].[NH4+]>C1COCC1>[CH3:20][O:19][C:17]1[CH:16]=[CH:15][C:14]([C:21]([C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[C:28]([O:33][CH3:34])[CH:29]=3)[CH:24]=2)=[O:22])=[C:13]([O:11][N:10]=[C:8]([CH3:9])[CH3:7])[CH:18]=1

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 67180Acetone, oximeHCID 22285703(2-Fluoro-4-methoxyphenyl)(6-methoxy-2-naphthyl)methanoneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 11451339Acetone O-[5-methoxy-2-(6-methoxy-2-naphthoyl)phenyl]oxime수율 95%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Potassium tert-butoxide (1.2 g, 10.6 mmol) was added into a solution of acetone oxime (0.78 g, 10.6 mmol) and THF (15 mL). After stirring for 1 h, (2-fluoro-4-methoxyphenyl)(6-methoxy-2-naphthyl)methanone (3.0 g, 9.7 mmol) in THF (3 mL) was added. The reaction mixture was refluxed for 3 h, then cooled to room temperature, poured into aqueous ammonium chloride, and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (hexanes/EtOAc 3/1) gave a brown solid (3.35 g, 95% yield, m.p. 117-118° C.); MS m/e 364 (M+).

후처리

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. extractionextracted with EtOAc
  3. dry with materialThe organic extracts were dried over MgSO4
  4. customEvaporation and purification by flash chromatography (hexanes/EtOAc 3/1)

출처 및 근거

ORD 기록
ord-a94c27bc4fce4a5093f6de465917248d
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06960607B2

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