(Diethylamino)sulfur trifluoride → 4-Fluoro-4-methyl-pent-2-ynoic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:11])[C:5]#[C:6][C:7](O)([CH3:9])[CH3:8])[CH3:2].CCN(S(F)(F)[F:18])CC>ClCCl>[CH2:1]([O:3][C:4](=[O:11])[C:5]#[C:6][C:7]([F:18])([CH3:9])[CH3:8])[CH3:2]Participants
4
Conditions
- Temperature
- -78 °C
Procedure
A solution of 4-hydroxy-4-methyl-pent-2-ynoic acid ethyl ester (4.9 g, 155 mmol) in dichloromethane (30 mL) was cooled to −78° C. and treated with DAST (5.3 g, 161.2 mmol) the reaction mixture was stirred for 2 h at −78° C. then warmed to room temperature and poured over ice. After the ice had melted, the phases were separated and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried (sodium sulfate) and concentrated on a rotary evaporator to provide 5.0 g (100%) of 4-fluoro-4-methyl-pent-2-ynoic acid ethyl ester as a brown oil.
Workup
- temperaturethen warmed to room temperature
- additionpoured over ice
- customthe phases were separated
- extractionthe aqueous phase was extracted with dichloromethane
- dry with materialThe combined organic phases were dried (sodium sulfate)
- concentrationconcentrated on a rotary evaporator
Sources & evidence
- ORD record
- ord-6077568ff76a4ae0abc333116b07213c
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07592353B2
Reaction notes
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