Hydrochloric Acid → 4-[4-(cyclopropylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one

HRID 1881815ノート

反応式

HRID 1881815 の反応式
[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)=[CH2:28].Cl>O1CCCC1>[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](=[O:15])[CH:27]=[CH2:28])=[CH:9][CH:8]=2)(=[O:5])=[O:6])[CH2:2][CH2:3]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 593315972-[4-(cyclopropylsulfonyl)phenyl]-N-methoxy-N-methyl-3-(tetrahydro-2H-pyran-4-yl)propanamideHCID 178418507HCID 178418507、化合物

生成物 1

HCID 593312584-[4-(cyclopropylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one収率 46%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-[4-(cyclopropylsulfonyl)phenyl]-N-methoxy-N-methyl-3-(tetrahydro-2H-pyran-4-yl)propanamide (10.2 g) in tetrahydrofuran (100 mL) was added dropwise vinylmagnesium bromide (1.0M tetrahydrofuran solution, 73 mL) under ice-cooling. The reaction mixture was stirred overnight at room temperature, 1M hydrochloric acid (80 mL) was added and the mixture was further 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 (4.25 g, yield 46%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio). melting point 92-93° C. MS: 349 (MH+).

後処理

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 30 min
  3. extractionThe reaction 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

出典と根拠

ORDレコード
ord-b3115777b023494792c5168f2254f2ab
出典データセット
uspto-grants-2012_11
特許番号
US08318746B2

反応ノート

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