Potassium Carbonate → (2S)-3,3-dimethyl-1-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-2-butanol

HRID 1182302노트

반응식

HRID 1182302 반응식
[C:1]([C@H:5]1[CH2:9]OS(=O)(=O)[O:6]1)([CH3:4])([CH3:3])[CH3:2].[F:12][C:13]([F:20])([F:19])[C:14]1[CH:18]=[CH:17][NH:16][N:15]=1.C(=O)([O-])[O-].[K+].[K+].C(Cl)(=O)C.CO.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:2][C:1]([CH3:4])([CH3:3])[C@H:5]([OH:6])[CH2:9][N:16]1[CH:17]=[CH:18][C:14]([C:13]([F:20])([F:19])[F:12])=[N:15]1

참가 물질

7

반응물 5

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 18070343-(Trifluoromethyl)pyrazoleHCID 22256297Acetyl chloride methanolHCID 58981698(4S)-4-tert-butyl-1,3,2-dioxathiolane 2,2-dioxide

생성물 1

HCID 69513260(2S)-3,3-dimethyl-1-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-2-butanol수율 56.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To 999.9 mg (5.55 mmol) of (4S)-4-tert-butyl-1,3,2-dioxathiolane 2,2-dioxide in 18 mL of N,N-dimethylformamide was added 755.0 mg (5.55 mmol) of 3-(trifluoromethyl)-1H-pyrazole. Then, 805.2 mg (5.83 mmol) of potassium carbonate was added, and the mixture was heated at 100° C. for 22 h. The resulting solution was cooled and 20 mL of acetyl chloride:methanol (1:9) were added. The reaction mixture was stirred for 2 h, and then saturated aqueous sodium bicarbonate was added. The mixture was extracted with ethyl acetate, and the extract was dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel column chromatography eluting with an ethyl acetate:hexanes solution (1:4) to give 736.5 mg (56%) of (2S)-3,3-dimethyl-1-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-2-butanol and a small amount of the other regioisomer. Rf=0.23 (1:4 ethyl acetate:hexanes); 1H-NMR (300 MHz, DMSO-d6): δ 7.90 (s, 1H), 6.65 (d, J=2 Hz, 1H), 4.93 (br s, 1H), 4.30 (dd, J=14 Hz, J=2 Hz, 1H), 3.96 (dd, J=14 Hz, 10 Hz, 1H), 3.45 (d, J=10 Hz, 1H), 0.90 (s, 9H); ES-LCMS m/z 237 (M+H).

후처리

  1. temperatureThe resulting solution was cooled
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe extract was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with an ethyl acetate

출처 및 근거

ORD 기록
ord-ac66a574e65b4126bb07754291f2a97d
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07288541B2

반응 노트

불러오는 중…