Ethanol → HCID 12369310, compound
Reaction equation
C(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.C(N(CC)CC)C.[CH3:16][C:17](=[O:20])[CH:18]=[CH2:19].[CH2:21]([OH:23])C>[Br-].C([N+]1C(C)=C(CCO)SC=1)C>[N:4]1[CH:3]=[CH:2][CH:7]=[CH:6][C:5]=1[C:21](=[O:23])[CH2:19][CH2:18][C:17](=[O:20])[CH3:16]Participants
6
Conditions
- Temperature
- 80 °C
Procedure
In a sealable vial were added nicotinaldehyde (4.7 g, 43.9 mmol), triethylamine (12.17 mL, 87 mmol), but-3-en-2-one (3.97 mL, 43.7 mmol), and 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazol-3-ium bromide (2.202 g, 8.73 mmol) in ethanol (10 mL). The reaction mixture was heated at 80° C. for 16 h. The reaction was then concentrated. The residue was treated with 1N HCl and extracted with DCM (3×20 mL). The organic layer was dried with Na2SO4. The crude product was added to a 80 g ISCO silica gel column and was purified with a gradient of 0% to 100% ethyl acetate in hexanes. Collection and concentration of pertinent fractions resulted in isolation of 1-(pyridin-2-yl)pentane-1,4-dione (4.5 g, 58%) as a tan liquid.
Workup
- concentrationThe reaction was then concentrated
- additionThe residue was treated with 1N HCl
- extractionextracted with DCM (3×20 mL)
- dry with materialThe organic layer was dried with Na2SO4
- additionThe crude product was added to a 80 g ISCO silica gel column
- customwas purified with a gradient of 0% to 100% ethyl acetate in hexanes
- customCollection and concentration of pertinent fractions
Sources & evidence
- ORD record
- ord-dd613f248b184db08df718e28848b44a
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08674115B2
Reaction notes
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