Dimethylformamide → HCID 86658573, 화합물

HRID 1520221

반응식

HRID 1520221 반응식
C([Li])CCC.C(NC(C)C)(C)C.[Li+].CC([N-]C(C)C)C.[CH3:21][O:22][C:23]1[CH:39]=[CH:38][C:26]([CH2:27][N:28]2[CH:32]=[C:31]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:30]=[N:29]2)=[CH:25][CH:24]=1.CN(C)[CH:42]=[O:43]>C1COCC1.CCOC(C)=O>[CH:42]([C:32]1[N:28]([CH2:27][C:26]2[CH:25]=[CH:24][C:23]([O:22][CH3:21])=[CH:39][CH:38]=2)[N:29]=[CH:30][C:31]=1[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:43]

참가 물질

8

반응물 5

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 44558860ethyl 1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylateHCID 178418339Butyllithium

생성물 1

HCID 86658573HCID 86658573, 화합물수율 60.2%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

According to Scheme 17 Step 1: Butyl lithium 2.5 M (16.9 mmol, 8.45 mL) was added to a solution of diisopropylamine (16.9 mmol, 2.37 mL) in THF (10 mL) at −78° C. and the reaction mixture was stirred at −78° C. for 5 minutes and then at room temperature. To the resulting LDA solution was added at −78° C. a solution of ethyl 1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylate (7.68 mmol, 2 g) in THF (30 mL) and the reaction mixture was stirred for 5 minutes at −78° C. N,N-Dimethylformamide (61.5 mmol, 4.73 mL) was added and then the reaction mixture was stirred at room temperature. The reaction mixture was diluted with AcOEt and was washed with a saturated aqueous solution of NH4Cl. The combined organic phases were dried over MgSO4, were filtered and were evaporated. The crude mixture was purified by flash chromatography over silica gel using cyclohexane/AcOEt (100:0 to 80:20) as eluent to yield ethyl 5-formyl-1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylate (4.62 mmol, 1.33 g, 60%).

후처리

  1. customat room temperature
  2. stirringthe reaction mixture was stirred for 5 minutes at −78° C
  3. stirringthe reaction mixture was stirred at room temperature
  4. washwas washed with a saturated aqueous solution of NH4Cl
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. filtrationwere filtered
  7. customwere evaporated
  8. customThe crude mixture was purified by flash chromatography over silica gel

출처 및 근거

ORD 기록
ord-06e583d12ffe451b9a33754eabef4349
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073907B2

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