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

HRID 262347노트

반응식

HRID 262347 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c0ea270cdfa84828a036c33256e41029
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04153799

반응 노트

불러오는 중…