Diethyl Ether → HCID 58125491, 화합물

HRID 1697463노트

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HRID 1697463 반응식
CON(C)[C:4]([C:6]1[CH:7]=[N:8][N:9]2[CH2:14][CH2:13][CH2:12][O:11][C:10]=12)=[O:5].[CH3:16][Mg]Br.CCOCC>O1CCCC1>[N:8]1[N:9]2[C:10]([O:11][CH2:12][CH2:13][CH2:14]2)=[C:6]([C:4](=[O:5])[CH3:16])[CH:7]=1

참가 물질

5

반응물 3

HCID 3283Diethyl Ether2회HCID 58125481HCID 58125481, 화합물HCID 178418573HCID 178418573, 화합물2회

생성물 1

HCID 58125491HCID 58125491, 화합물수율 82%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

A solution of 6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-3-carboxylic acid methoxy-methyl-amide (9.02 g, 42.7 mmol) in tetrahydrofuran (300 mL) was cooled to 0° C. 3 M methylmagnesium bromide in ether (15.3 mL, 43 mmol) was added and the reaction was stirred at 0° C. for 30 minutes, then warmed to room temperature. Additional 3 M methylmagnesium bromide in ether (15.3 mL, 43 mmol) was added after 1 hour, and the mixture was stirred at room temperature overnight, then the volatiles were removed in vacuo. The residue was partitioned between EtOAc (100 mL) and saturated NaHCO3 solution (150 mL). The aqueous layer was extracted with EtOAc (2×100 mL), and the combined organic layers were washed with brine (3×50 mL), dried (Na2SO4), filtered and concentrated. Flash chromatography (0 to 4% MeOH in DCM) afforded the ketone (5.79 g, 82%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ7.69 (s, 1H), 4.44 (t, 2H, J=5.25 Hz), 4.09 (t, 2H, J=6.10 Hz), 2.23 (s, 3H), 2.22-2.17 (m, 2H).

후처리

  1. temperaturewarmed to room temperature
  2. stirringthe mixture was stirred at room temperature overnight
  3. customthe volatiles were removed in vacuo
  4. customThe residue was partitioned between EtOAc (100 mL) and saturated NaHCO3 solution (150 mL)
  5. extractionThe aqueous layer was extracted with EtOAc (2×100 mL)
  6. washthe combined organic layers were washed with brine (3×50 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-1e464bfc4fce4477bf0eeff6b15e8570
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163901B2

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