Cesium carbonate → Methyl 5-((tert-butyldimethylsilyloxy)methyl)-3-phenylthiophene-2-carboxylate

HRID 1186711ノート

反応式

HRID 1186711 の反応式
[Si:1]([O:8][CH2:9][C:10]#[C:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:20]([O:24][CH3:25])(=[O:23])[CH2:21][SH:22].S([O-])([O-])(=O)=O.[Mg+2].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.CO>[Si:1]([O:8][CH2:9][C:10]1[S:22][C:21]([C:20]([O:24][CH3:25])=[O:23])=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 16907Methyl ThioglycolateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 108695084-{[Tert-butyl(dimethyl)silyl]oxy}-1-phenylbut-2-yn-1-one

生成物 1

HCID 66863649Methyl 5-((tert-butyldimethylsilyloxy)methyl)-3-phenylthiophene-2-carboxylate

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 167 (8.924 g, 32.5 mmol) in THF was added methyl thioglycolate (4.36 mL, 48.8 mmol) and stirred 2 hours at room temperature. MAGNESIUM SULFATE (3.91 g, 32.5 mmol) was added and the reaction mixture was stirred for 1 hour. Then CESIUM CARBONATE (10.60 g, 32.5 mmol) in 30 mL of MeOH was added and stirred for an additional 2 hours at room temperature. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with brine, dried over sodium sulfate and filtered. The solvent was evaporated and the residue was purified by silica gel chromatography (0%-5% ethyl acetate in hexanes) to yield 168 in 54% (6.389 g) as an orange solid

後処理

  1. stirringthe reaction mixture was stirred for 1 hour
  2. stirringstirred for an additional 2 hours at room temperature
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customThe solvent was evaporated
  10. customthe residue was purified by silica gel chromatography (0%-5% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-831f253868a741158a66a8f91f556976
出典データセット
uspto-grants-2014_03
特許番号
US08673911B2

反応ノート

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