Toluene → Methyl 2-(4-acetyl-5-methyl-1H-pyrazol-1-yl)acetate

HRID 2425547노트

반응식

HRID 2425547 반응식
[C:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:10][C:11]([OH:13])=[O:12])[C:8]=1[CH3:9])(=[O:3])[CH3:2].[C:14]1(C)C=CC=CC=1.C[Si](C=[N+]=[N-])(C)C.CCOCC>CO>[C:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[C:8]=1[CH3:9])(=[O:3])[CH3:2]

참가 물질

6

반응물 4

HCID 1140TolueneHCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 632769652-(4-acetyl-5-methyl-1H-pyrazol-1-yl)acetic acid

생성물 1

HCID 67181907Methyl 2-(4-acetyl-5-methyl-1H-pyrazol-1-yl)acetate수율 99%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 2-(4-acetyl-5-methyl-1H-pyrazol-1-yl)acetic acid (1.17 g, 6.42 mmol, as a mixture of regioisomers from the previous step) in MeOH (8.8 ml)-Toluene (30.6 ml) was added a 2 M solution of (trimethylsilyl)diazomethane in ether (4.8 ml, 9.6 mmol) dropwise at 0° C. The resulting solution was allowed to warm to rt and stirred for 120 min. The reaction was quenched by addition of AcOH (3 ml) and the solvent was concentrated in vacuo. The crude product was purified by silica gel column chromatography (CH2Cl2:MeOH=30:1) to give the desired product along with a mixture of regioisomers (>99% yield). 1H NMR (270 MHz, CDCl3) δ 2.45 (3H, s), 2.53 (3H, s), 3.79 (3H, s), 4.90 (2H, s), 7.88 (1H, s).

후처리

  1. customThe reaction was quenched by addition of AcOH (3 ml)
  2. concentrationthe solvent was concentrated in vacuo
  3. customThe crude product was purified by silica gel column chromatography (CH2Cl2:MeOH=30:1)

출처 및 근거

ORD 기록
ord-482840abe9c74daa8b9da94f887c52c0
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07964732B2

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