Reaction equation
[C-:1]#[N:2].[K+].[F:4][C:5]([F:18])([C:14]([F:17])([F:16])[F:15])[C:6](=[O:13])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].S(=O)(=O)(O)O>O.CCO>[C:1]([C:6]([OH:13])([C:5]([F:18])([F:4])[C:14]([F:15])([F:16])[F:17])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])#[N:2]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
A solution of KCN (1.4 eq.) in water (0.5 M) was added with stirring to an ice-cooled solution of ethyl 4,4,5,5,5-pentafluoro-3-oxopentanoate (1 eq.) in EtOH and water (40:60 vol). The mixture was stirred for 6 h at 0° C. and then acidified with 6N sulphuric acid and extracted with Et2O. The organic phase was dried (Na2SO4), and the solvents were removed under reduced pressure. The residue was vacuum distilled. The product fraction was collected at 74-76° C./0.5 mbar. (400 MHz, CDCl3) δ: 5.88 (1H, s), 4.40-4.23 (2H, m), 3.04 (1H, s), 1.33 (3H, t, J=7.1 Hz).
Workup
- extractionextracted with Et2O
- dry with materialThe organic phase was dried (Na2SO4)
- customthe solvents were removed under reduced pressure
- distillationdistilled
- customThe product fraction was collected at 74-76° C./0.5 mbar
Sources & evidence
- ORD record
- ord-8896f9ccbbb048a8acabd0b92b467d4a
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08268827B2
Linked notes
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