Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl- → methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-hydroxy-2,2,5-trimethylhexanoate

HRID 563413ノート

反応式

HRID 563413 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17](=[O:22])[CH2:18][CH:19]([CH3:21])[CH3:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH3:23][O:24][C:25]([O:29][Si](C)(C)C)=[C:26]([CH3:28])[CH3:27]>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([OH:22])([CH2:18][CH:19]([CH3:20])[CH3:21])[C:26]([CH3:28])([CH3:27])[C:25]([O:24][CH3:23])=[O:29])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 552336Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-HCID 670054831-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-methylbutan-1-one

生成物 1

HCID 59252801methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-hydroxy-2,2,5-trimethylhexanoate収率 95%

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

1-(1-(4-Fluorophenyl)-1H-indazol-5-yl)-3-methylbutan-1-one (220 mg, 0.742 mmol) was dissolved in 10 mL of dry DCM and 1-methoxy-2-methyl-1-(trimethylsiloxy)propene (0.162 mL, 0.8 mmol) was added. The reaction mixture was cooled to 0° C. and TiCl4 (0.8 mL of 1.0 M DCM solution, 0.8 mmol) was added portionwise and then stirred 12 h. The reaction was quenched with aqueous sodium bicarbonate and extracted 2×DCM. The organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified SiO2 chromatography eluting with 1:1 EtOAc/hexane to give 280 mg (95% yield) of methyl 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-hydroxy-2,2,5-trimethylhexanoate. MS found: (M+H)+=399.

後処理

  1. customThe reaction was quenched with aqueous sodium bicarbonate
  2. extractionextracted 2×DCM
  3. dry with materialThe organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified SiO2 chromatography
  7. washeluting with 1:1 EtOAc/hexane

出典と根拠

ORDレコード
ord-a3d066bba62944deb71c34b5c0901fa6
出典データセット
uspto-grants-2011_11
特許番号
US08067447B2

反応ノート

読み込み中…