Sodium Hydroxide → 5-(3-methylbutyl)-1H-pyrazole-3-carboxylic Acid

HRID 1366904노트

반응식

HRID 1366904 반응식
[OH-].[Na+].C([O:5][C:6]([C:8]1[CH:12]=[C:11]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[NH:10][N:9]=1)=[O:7])C>CO>[CH3:16][CH:15]([CH3:17])[CH2:14][CH2:13][C:11]1[NH:10][N:9]=[C:8]([C:6]([OH:7])=[O:5])[CH:12]=1

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 574350915-(3-methylbutyl)-1H-pyrazole-3-carboxylic Acid Ethyl Ester

생성물 1

HCID 118456535-(3-methylbutyl)-1H-pyrazole-3-carboxylic Acid수율 97.6%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Freshly prepared aq. NaOH (10 M in H2O, 80.85 mmol) was added to a stirring, room temperature solution of 47 (3.40 g, 16.17 mmol) in MeOH (40.4 mL, 0.4 M) under N2. The reaction was then heated to reflux until the reaction was judged complete by HPLC (6 min): The reaction was concentrated and then dissolved in 14 mL H2O. 10% aq. HCl was added dropwise until the pH=2. The white solid that precipitated from the reaction was filtered off and washed with cold H2O. The solid was dried under vacuum overnight to obtain 2.8753 g (97.6%) of 48. (Note: An undesired impurity has a retention time of 9.522 min by HPLC). 1H (CDCl3, 400 MHz): δ 6.61 (1H, s), 2.70 (2H, t, J=7.8 Hz), 1.63-1.51 (3H, m), 0.94 (6H, d, J=6.3 Hz) ppm. 13C (CDCl3, 100 MHz): δ 164.35, 149.48, 143.00, 107.34, 39.35, 28.71, 24.69, 22.65 ppm. DEPT (CDCl3, 100 MHz): CH3 carbons: 22.65; CH2 carbons: 39.35, 24.69; CH carbons: 107.34, 28.71 ppm. HPLC: 9.522 min.

후처리

  1. temperatureThe reaction was then heated
  2. temperatureto reflux until the reaction
  3. customwas judged complete by HPLC (6 min)
  4. concentrationThe reaction was concentrated
  5. dissolutiondissolved in 14 mL H2O
  6. addition10% aq. HCl was added dropwise until the pH=2
  7. customThe white solid that precipitated from the reaction
  8. filtrationwas filtered off
  9. washwashed with cold H2O
  10. customThe solid was dried under vacuum overnight

출처 및 근거

ORD 기록
ord-2ce51349d8ce43cdb1020bd6d65db8db
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893098B2

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