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

HRID 1186711노트

반응식

HRID 1186711 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-831f253868a741158a66a8f91f556976
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673911B2

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