p-Toluenesulfonic acid monohydrate → 1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-3-nitro-1H-pyrazole

HRID 2381285노트

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HRID 2381285 반응식
[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:9][C@H:10]([OH:13])[CH2:11][OH:12])[N:5]=1)([O-:3])=[O:2].O.[C:15]1(C)[CH:20]=CC(S(O)(=O)=O)=C[CH:16]=1>COC(OC)(C)C.O1CCCC1>[CH3:16][C:15]1([CH3:20])[O:13][C@@H:10]([CH2:9][N:6]2[CH:7]=[CH:8][C:4]([N+:1]([O-:3])=[O:2])=[N:5]2)[CH2:11][O:12]1

참가 물질

5

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 59344949(S)-3-(3-nitro-1h-pyrazol-1-yl)propane-1,2-diol

생성물 1

HCID 593449571-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-3-nitro-1H-pyrazole수율 269.1%

시약·촉매·용매 2

HCID 64952,2-Dimethoxypropane용매HCID 8028Tetrahydrofuran용매

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온도
25 °C

실험 절차

A solution of (S)-3-(3-nitro-pyrazol-1-yl)-propane-1,2-diol (1 g, 5.34 mmol) in 2,2-dimethoxypropane (8.5 mL, 0.63M) and tetrahydrofuran (10 mL, 0.53 M) was treated with para-toluenesulfonic acid monohydrate (0.11 g, 0.57 mmol). The reaction was stirred under nitrogen at 25° C. overnight. After this time, the reaction was concentrated in vacuo. Silica gel column chromatography (Aspire 40 g, 20-45% ethyl acetate/hexanes) afforded 1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-3-nitro-1H-pyrazole (348.5 mg, 29%) as a viscous yellow/orange oil. The material was used without further purification.

후처리

  1. concentrationAfter this time, the reaction was concentrated in vacuo

출처 및 근거

ORD 기록
ord-79854ee0ff2b491bb184140fb64207a7
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08258134B2

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