Methanol → Methyl 4,4,4-trifluoro-2-hydroxybutanoate
Reaction equation
S(Cl)(Cl)=O.[F:5][C:6]([F:14])([F:13])[CH2:7][CH:8]([OH:12])[C:9]([OH:11])=[O:10].[CH3:15]O>>[F:5][C:6]([F:14])([F:13])[CH2:7][CH:8]([OH:12])[C:9]([O:11][CH3:15])=[O:10]Participants
4
Conditions
- Temperature
- 70 °C
Procedure
Thionyl chloride (0.139 ml, 1.90 mmol) was added dropwise to a solution of 12-2 (200 mg, 1.27 mmol) in MeOH (2 ml) at room temperature. After addition was complete, the reaction was heated in a sealed vessel at 70° C. for 2 h. The reaction was cooled to room temperature and concentrated in vacuo. The residue was diluted with 7N NH3/MeOH (3 mL) and filtered to remove insolubles. The filtrate was concentrated to dryness to afford 12-3 as a clear oil.
Workup
- additionAfter addition
- temperatureThe reaction was cooled to room temperature
- concentrationconcentrated in vacuo
- additionThe residue was diluted with 7N NH3/MeOH (3 mL)
- filtrationfiltered
- customto remove insolubles
- concentrationThe filtrate was concentrated to dryness
Sources & evidence
- ORD record
- ord-19cf1507efbc4fac9d15401883d302ed
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428492B2
Reaction notes
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