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

HRID 1901761ノート

反応式

HRID 1901761 の反応式
[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]

参加物

5

反応物 3

HCID 9590p-FluoronitrobenzeneHCID 233686093,3-dimethyl-5-[1,2,4-triazol-1-ylmethyl]-3H-isobenzofuran-1-one2 回HCID 23665647Potassium tert-butoxide

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2234c574978e42ff904f7d43ff18981b
出典データセット
uspto-grants-1996_11
特許番号
US05578630

反応ノート

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