p-Fluoronitrobenzene → 5-[(4-nitrophenyl)-1,2,4-triazol-1-ylmethyl]-3,3-dimethyl-3H-isobenzofuran-1-one

HRID 1901761노트

반응식

HRID 1901761 반응식
[CH3:1][C:2]1([CH3:18])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:11][N:12]3[CH:16]=[N:15][CH:14]=[N:13]3)[CH:9]=2)[C:4](=[O:17])[O:3]1.CC(C)([O-])C.[K+].F[C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1>CN(C)C=O>[N+:32]([C:29]1[CH:30]=[CH:31][C:26]([CH:11]([N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[C:4](=[O:17])[O:3][C:2]3([CH3:18])[CH3:1])=[CH:27][CH:28]=1)([O-:34])=[O:33]

참가 물질

5

반응물 3

HCID 9590p-FluoronitrobenzeneHCID 233686093,3-dimethyl-5-[1,2,4-triazol-1-ylmethyl]-3H-isobenzofuran-1-one2회HCID 23665647Potassium tert-butoxide

생성물 1

HCID 233686115-[(4-nitrophenyl)-1,2,4-triazol-1-ylmethyl]-3,3-dimethyl-3H-isobenzofuran-1-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

3,3-Dimethyl-5-[1,2,4-triazol-1-ylmethyl]-3H-isobenzofuran-1-one (200 mg, Intermediate 1) was dissolved in N,N-dimethylformamide (8 ml) at 0° under nitrogen and potassium tert-butoxide was added (138 mg). After 30 minutes 4-fluoronitrobenzene (232 mg) in N,N-dimethylformamide (1 ml) was added and stirring continued for one hour. The mixture was warmed to room temperature, stirred for one hour then partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate then the combined organic extracts were washed with water, brine, dried then evaporated to a yellow solid. The crude material was purified by column chromatography on Merck 9385 silica eluting with dichloromethane:methanol (50:1) to give a yellow oil, 5-[(4-nitrophenyl)-1,2,4-triazol-1-ylmethyl]-3,3-dimethyl-3H-isobenzofuran-1-one.

후처리

  1. stirringstirred for one hour
  2. customthen partitioned between water and ethyl acetate
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined organic extracts were washed with water, brine
  5. customdried
  6. customthen evaporated to a yellow solid
  7. customThe crude material was purified by column chromatography on Merck 9385 silica eluting with dichloromethane:methanol (50:1)

출처 및 근거

ORD 기록
ord-2234c574978e42ff904f7d43ff18981b
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05578630

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