1-Butanol → Butyl 3,3,3-trifluoro-2,2-dimethylpropanoate
Reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([CH3:8])([CH3:7])[C:4]([OH:6])=[O:5].C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[CH2:24](O)[CH2:25][CH2:26][CH3:27]>C(Cl)Cl.CN(C=O)C>[CH2:24]([O:5][C:4](=[O:6])[C:3]([CH3:8])([CH3:7])[C:2]([F:10])([F:9])[F:1])[CH2:25][CH2:26][CH3:27]Participants
7
Procedure
3,3,3-Trifluoro-2,2-dimethyl-propionic acid (3.0 g, 19.2 mmol) and a drop of DMF are dissolved in 30 mL of DCM and treated dropwise at RT with oxalyl chloride (1.85 mL, 21.1 mmol). After 2 h gas evolution ceases and the mixture is treated slowly with triethyl amine (5.36 mL, 38.4 mmol) followed by n-butanol (2.1 mL, 23 mmol). The mixture is stirred over night, the solvent evaporated and the residue stirred with hexanes. The solid is filtered off and the filtrate is evaporated to a brown-red oil. Kugelrohr distillation (10 mbar, 60-80° C. oven temperature) gives the title compound a colorless liquid.
Workup
- customthe solvent evaporated
- stirringthe residue stirred with hexanes
- filtrationThe solid is filtered off
- customthe filtrate is evaporated to a brown-red oil
- distillationKugelrohr distillation (10 mbar, 60-80° C. oven temperature)
Sources & evidence
- ORD record
- ord-06f6d7056e584c06870e6d37842539a8
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08476268B2
Reaction notes
Loading…