Triethylsilane → 4-(5-(Ethoxycarbonyl)-1H-pyrrol-3-yl)butanoic acid
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:10][CH:9]=[C:8]([C:11](=O)[CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:7]=1)=[O:5])[CH3:2].C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[CH2:1]([O:3][C:4]([C:6]1[NH:10][CH:9]=[C:8]([CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])[CH:7]=1)=[O:5])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Into a 2000-mL 4-necked round-bottom flask was placed a solution of 113g (105 g, 438.92 mmol, 1.00 equiv) in CF3COOH (1000 mL), followed by the addition of triethylsilane (204 g, 1.75 mol, 4.00 equiv) dropwise with stirring at room temperature over 30 min (FIG. 14). The resulting solution was stirred at room temperature for 8 h, concentrated under vacuum and diluted with 500 mL of water and 500 mL of ethyl acetate. The pH value of the solution was adjusted to 7 with saturated aqueous sodium bicarbonate. The resulting solution was extracted with 3×500 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to afford 30 g (30%) of 113h as a light brown solid.
Workup
- customInto a 2000-mL 4-necked round-bottom flask was placed
- stirringThe resulting solution was stirred at room temperature for 8 h
- concentrationconcentrated under vacuum
- additiondiluted with 500 mL of water and 500 mL of ethyl acetate
- extractionThe resulting solution was extracted with 3×500 mL of ethyl acetate
- dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-7a955e6ec04445988790a06989191479
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08729072B2
Reaction notes
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