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

HRID 1186711Notes

Reaction equation

HRID 1186711 reaction equation
[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]

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

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

Workup

  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)

Sources & evidence

ORD record
ord-831f253868a741158a66a8f91f556976
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

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