Bromide ion → 1-(Pyridin-2-yl)hept-6-en-3-one

HRID 579528

반응식

HRID 579528 반응식
CON(C)[C:4](=[O:13])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.[Br-].[Cl-].[Na+]>O1CCCC1>[N:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH2:6][CH2:5][C:4](=[O:13])[CH2:7][CH2:6][CH:5]=[CH2:4]

참가 물질

5

반응물 3

HCID 259Bromide ionHCID 5234Sodium ChlorideHCID 78981096N-methoxy-N-methyl-3-(pyridin-2-yl)propanamide

생성물 1

HCID 668331331-(Pyridin-2-yl)hept-6-en-3-one수율 169.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

While under a nitrogen atmosphere, a solution of N-methoxy-N-methyl-3-(pyridin-2-yl)propanamide (1.00 g, 5.15 mmol), in tetrahydrofuran (10 mL) was cooled to 0° C. and treated with 4-butenylmagnesiun bromide (0.5 M in THF, 16 mL, 8.0 mmol) in a dropwise manner. The solution was stirred for 1 hour at 0° C. then allowed to warm to room temperature for 3 h. The resulting solution was poured into saturated aqueous sodium chloride (100 mL) and extracted with ethyl acetate (3×50 mL). The combined organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated. Purification by flash column chromatography (silica gel, 0-25% ethyl acetate in heptane) gave 1-(pyridin-2-yl)hept-6-en-3-one as a colorless oil (828 mg, 85%). ESI MS found for C12H15NO m/z [190.1 (M+1)].

후처리

  1. temperatureto warm to room temperature for 3 h
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe combined organic phase was washed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography (silica gel, 0-25% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-8dbc8efa3b884123afc376f600b34d03
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040703B2

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