Acetic Anhydride → HCID 15718999, compound
Reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[N:8]1[CH:13]=[CH:12][C:11](CCO)=[CH:10][CH:9]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CC=CN=1)C>[C:5]([O:4][CH2:1][CH2:2][C:11]1[CH:12]=[CH:13][N:8]=[CH:9][CH:10]=1)(=[O:7])[CH3:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 11.3 ml of acetic anhydride in 100 ml of methylene chloride was added approximately 125 mg of dimethylaminopyridine, and the solution was cooled to 0° C. In a separate container 12.2 g (0.099 mol) of 4-pyridineethanol was suspended in 80 ml of methylene chloride and 12.14 g (0.120 mol, 16.7 ml) of triethylamine was added. This mixture was added to the acetic anhydride solution slowly by pipet. The resulting mixture was stirred at room temperature for approximately 90 minutes and quenched with about 100 ml of water. The mixture was placed in a separatory funnel and the organic layer was isolated and washed two times with 100 ml portions of water. The aqueous layers were combined and extracted two times with methylene chloride and one time with diethyl ether. The organic extracts were combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to provide 16.2 g of the desired compound. Purification by high pressure liquid chromatography provided 11.19 g of 4-pyridineethanol acetate.
Workup
- customquenched with about 100 ml of water
- customThe mixture was placed in a separatory funnel
- customthe organic layer was isolated
- washwashed two times with 100 ml portions of water
- extractionextracted two times with methylene chloride and one time with diethyl ether
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-f114c3e8c97b444f9bd35e0466dec931
- Source dataset
- uspto-grants-1990_11
- Patent number
- US04968678
Reaction notes
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