Ethyl Acetate → Ethyl 2-(fluoromethyl)prop-2-enoate
Reaction equation
O[CH2:2][C:3](=[CH2:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].CCN(S(F)(F)[F:16])CC.C([O-])(O)=O.[Na+].C(OCC)(=O)C>C(Cl)Cl>[F:16][CH2:2][C:3](=[CH2:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5]Participants
6
Conditions
- Temperature
- -78 °C
Procedure
To a solution of ethyl 2-(hydroxymethyl)acrylate (5 g, 38 mmol) in 50 mL of methylene chloride was added DAST (6.0 mL, 46.1 mmol) at −78° C. The reaction mixture was stirred at −78° C. for 1 h, then warmed up to room temperature and continuously stirred overnight. 20 mL of saturated NaHCO3 aqueous solution and 20 mL of ethyl acetate were added to quench the reaction. The organic layer was separated, and the aqueous layer was extracted twice with EtOAc (20 ml×2). The combined organic extracts were dried over MgSO4 and evaporated to give an oil residue (2.8 g, yield: 56%). MS (m/z): 131 (M−1-1)+.
Workup
- temperaturewarmed up to room temperature and continuously stirred overnight
- customto quench
- customthe reaction
- customThe organic layer was separated
- extractionthe aqueous layer was extracted twice with EtOAc (20 ml×2)
- dry with materialThe combined organic extracts were dried over MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-4ad7d4e4f3174834ad95ffc8e13434e3
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08729063B2
Reaction notes
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