Pyridine → 5,5-Dimethyl-4-(4-(methylsulfonyl)phenyl)-3-(4-methoxyphenyl)-2-(5H)-furanone

HRID 325178

反応式

[OH:1][C:2]([CH3:16])([CH3:15])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1)=O.N1C=CC=CC=1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32](Cl)=[O:33])=[CH:27][CH:26]=1.C1CCN2C(=NCCC2)CC1>C(Cl)Cl.CCOC(C)=O.Cl>[CH3:15][C:2]1([CH3:16])[O:1][C:32](=[O:33])[C:31]([C:28]2[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)=[C:3]1[C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1

参加物

実験手順

To a cold solution (0° C.) of 2-hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)-propane-1-one (726 mg, 3.5 mmol, Step 3), pyridine (0.5 mL, 6.2 mmol) in CH2Cl2 (10 mL) was added 4-methoxyphenylacetyl chloride (1.5 g, 8.4 mmol) over 2 minutes. The resulting yellow solution was stirred at r.t. for 18 h. Then DBU was added in portions every 30 min. (3×1.0 mL, 3×6.7 mmol). The reaction was diluted with EtOAc (100 mL) and 1N HCl (50 mL). The organic layer was washed with water (50 mL), dried over MgSO4 and concentrated. The crude product was purified first by flash chromatography eluted with 40% EtOAc in hexane and then by crystallization in EtOAc and hexane (1:1, 26 mL) to give the title compound as a white solid.

後処理

washThe organic layer was washed with water (50 mL)
dry with materialdried over MgSO4
concentrationconcentrated
customThe crude product was purified first by flash chromatography
washeluted with 40% EtOAc in hexane
customby crystallization in EtOAc

出典と根拠

ORDレコード: ord-8ff12c79c6c343788b1af6fba6af283c
出典データセット: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US06222048B1

反応式

参加物

反応物 4

生成物 1

試薬・触媒・溶媒 3

実験手順

後処理

出典と根拠

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