Hydrochloric Acid → 2-[4-(cyclopropylsulfonyl)phenyl]-1-(tetrahydro-2H-pyran-4-yl)hex-4-en-3-one

HRID 1881847노트

반응식

HRID 1881847 반응식
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH2:20][CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[C:14](N(OC)C)=[O:15])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[CH:27]([Mg]Br)=[CH:28][CH3:29].Cl>O1CCCC1>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:14](=[O:15])[CH:27]=[CH:28][CH3:29])[CH2:20][CH:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 593315972-[4-(cyclopropylsulfonyl)phenyl]-N-methoxy-N-methyl-3-(tetrahydro-2H-pyran-4-yl)propanamideHCID 178456053HCID 178456053, 화합물

생성물 1

HCID 684311882-[4-(cyclopropylsulfonyl)phenyl]-1-(tetrahydro-2H-pyran-4-yl)hex-4-en-3-one수율 61%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-[4-(cyclopropylsulfonyl)phenyl]-N-methoxy-N-methyl-3-(tetrahydro-2H-pyran-4-yl)propanamide (1.00 g) in tetrahydrofuran (10 mL) was added 1-propenylmagnesium bromide (0.5M tetrahydrofuran solution, 17.2 mL) under ice-cooling, and the mixture was warmed to room temperature and stirred for 3 hr. The reaction mixture was poured into a mixture of concentrated hydrochloric acid (5 mL) and ice (100 g), and the mixture was stirred for 15 min. The 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 (632 mg, yield 61%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (4:1, volume ratio). MS: 363 (MH+).

후처리

  1. temperaturecooling
  2. stirringthe mixture was stirred for 15 min
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-717b76213c154864bbedb746a43fbb45
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318746B2

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