Hexane → HCID 59394508, 화합물

HRID 450303

반응식

HRID 450303 반응식
[CH3:1][C:2]1[N:3]([C:8]2[CH:12]=[CH:11][N:10]([CH3:13])[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[Li][CH2:15]CCC.CCCCCC.C([O:27][C:28](=O)[C:29]([F:32])([F:31])[F:30])C>C1COCC1>[CH3:7][C:4]1[N:3]([C:8]2[CH:12]=[C:11]([C:28]([OH:27])([CH3:15])[C:29]([F:32])([F:31])[F:30])[N:10]([CH3:13])[N:9]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

참가 물질

6

반응물 4

HCID 8058HexaneHCID 9794Ethyl trifluoroacetateHCID 132489953-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-pyrazoleHCID 178418339Butyllithium

생성물 1

HCID 59394508HCID 59394508, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 3-(2,5-dimethyl-pyrrol-1-yl)-1-methyl-1H-pyrazole (1.5 g, 8.6 mmol) in THF (100 mL) at −78° C., 2.5M nBuLi in Hexane (4.1 mL, 10.3 mmol) is added and stirred for 1.5 hours followed by the addition of trifluoro-acetic acid ethyl ester (1.5 g, 10.3 mmol). After 10 min the ice bath is removed and the reaction is allowed to reach room temperature. Then the reaction is cooled down to −78° C. again and methylmagnesium bromide (1.0 M solution in hexane, 8.6 mL) is added. After 5 min the ice bath is removed and the mixture is stirred at room temperature for 3 hour, poured into water, separated, and the water layer is extracted with DCM. The organic layers are combined and concentrated. The residue is purified by FCC to give the title compound. MS (ESI) m/z 288.1 (M+1).

후처리

  1. customAfter 10 min the ice bath is removed
  2. customto reach room temperature
  3. additionmethylmagnesium bromide (1.0 M solution in hexane, 8.6 mL) is added
  4. customAfter 5 min the ice bath is removed
  5. stirringthe mixture is stirred at room temperature for 3 hour
  6. additionpoured into water
  7. customseparated
  8. extractionthe water layer is extracted with DCM
  9. concentrationconcentrated
  10. customThe residue is purified by FCC

출처 및 근거

ORD 기록
ord-8b050758ce954648810539710139d43b
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486954B2

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