Sodium hydride → [2-[3,5-bis(Acetoxymethyl)pyrazol-1-yl]-5-nitrophenyl]phenyl methanone

HRID 262347

反応式

HRID 262347 の反応式
[C:1]([O:4][CH2:5][C:6]1[CH:10]=[C:9]([CH2:11][O:12][C:13](=[O:15])[CH3:14])[NH:8][N:7]=1)(=[O:3])[CH3:2].[H-].[Na+].F[C:19]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][C:20]=1[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:22]>CN(C=O)C>[C:13]([O:12][CH2:11][C:9]1[CH:10]=[C:6]([CH2:5][O:4][C:1](=[O:3])[CH3:2])[N:7]([C:19]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][C:20]=2[C:21]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:22])[N:8]=1)(=[O:15])[CH3:14]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 123775343,5-DiacetoxymethylpyrazoleHCID 12377535(2-Fluoro-5-nitrophenyl)(phenyl)methanone

生成物 1

HCID 12377536[2-[3,5-bis(Acetoxymethyl)pyrazol-1-yl]-5-nitrophenyl]phenyl methanone

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of 4.2 g. (20 mmol) of 3,5-diacetoxymethylpyrazole in 15 ml. of DMF was added dropwise to a suspension of 960 mg. (20 mmol) of NaH (50% in mineral oil) in 25 ml. of DMF stirred at 0° and under argon. After the evolution of H2 had ceased, 4.9 g. (20 mmol) of 2-fluoro-5-nitrobenzophenone was added in one portion. After stirring at 0° for 4 hours, the mixture was poured into ice-water and extracted with EtOAc. The organic phase was washed with dil. brine, dried (MgSO4) and concentrated. The residue was chromatographed on silica gel using benzene/EtOAc (1:1) as eluent. Removal of the solvents gave crude end product as a gum which was not purified further. The nmr (CDCl3) had signals at: δ2.00 (3H, s, CH3), 2.07 (3H, s, CH3), 4.82 (2H, s, CH2), 5.10 (2 H, s, CH2) 6.33 (1H, s, C=CH), and 7.30-8.67 (8H, m, C6H5 +C6H3).

後処理

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with dil. brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel
  6. customRemoval of the solvents
  7. customgave crude end product as a gum which
  8. customwas not purified further

出典と根拠

ORDレコード
ord-c0ea270cdfa84828a036c33256e41029
出典データセット
uspto-grants-1979_05
特許番号
US04153799

関連ノート

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