Hydrochloric Acid → 5-Cyclopentyl-4-[5-(methylsulfanyl)pyridin-2-yl]pent-1-en-3-one

HRID 1881945노트

반응식

HRID 1881945 반응식
[CH:1]1([CH2:6][CH:7]([C:14]2[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[CH:16][N:15]=2)[C:8](N(OC)C)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:22]([Mg]Br)=[CH2:23].Cl>O1CCCC1>[CH:1]1([CH2:6][CH:7]([C:14]2[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[CH:16][N:15]=2)[C:8](=[O:9])[CH:22]=[CH2:23])[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 593315843-cyclopentyl-N-methoxy-N-methyl-2-[5-(methylsulfanyl)pyridin-2-yl]propanamideHCID 178418507HCID 178418507, 화합물

생성물 1

HCID 593315425-Cyclopentyl-4-[5-(methylsulfanyl)pyridin-2-yl]pent-1-en-3-one수율 54%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 3-cyclopentyl-N-methoxy-N-methyl-2-[5-(methylsulfanyl)pyridin-2-yl]propanamide (350 mg) in tetrahydrofuran (4.5 mL) was cooled to 0° C., and vinylmagnesium bromide (1.0M tetrahydrofuran solution, 4.54 mL) was added dropwise thereto. The reaction mixture was stirred at room temperature for 1 hr, and poured into 1M hydrochloric acid, and the mixture was stirred for 30 min. The reaction mixture was extracted with ethyl acetate, and the ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (171 mg, yield 54%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio).

후처리

  1. stirringthe mixture was stirred for 30 min
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washthe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-42c6adb2678d4da08cc41d409765406e
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318746B2

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