Tributylstannane → Ethyl 2,2,5,5,5-pentafluoropentanoate
Reaction equation
I[CH:2]([C:12]([F:15])([F:14])[F:13])[CH2:3][C:4]([F:11])([F:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6].C([SnH](CCCC)CCCC)CCC>>[F:10][C:4]([F:11])([CH2:3][CH2:2][C:12]([F:13])([F:15])[F:14])[C:5]([O:7][CH2:8][CH3:9])=[O:6]Participants
3
Conditions
- Temperature
- 50 °C
Procedure
The compound ethyl 4-iodo-2,2,5,5,5-pentafluoropentanoate prepared from above experiment (86.5 g, 0.25 mol) was added dropwise into a well-stirred tributyltin hydride liquid (75.5 g, 0.26 mol). The reaction temperature was controlled at below 30° C. with external cooling during the process. After addition was complete, the mixture was stirred at 50° C. for 2 hr. The product was isolated by distillation, 42.0 g (76.4% yield) of product was obtained as a clear, colorless liquid, bp. 38-39° C./10 mm Hg. 1H NMR (500 MHz, CDCl3): δ 4.35 (q, J=7 Hz, 2H), 2.35 (m, 4H), 1.38 (t, J=7 Hz, 3H); 19F NMR (282.75 MHz, CDCl3): −67.3 (m, 3F), −107.5 (m, 2F).
Workup
- customwas controlled at below 30° C.
- temperaturewith external cooling during the process
- additionAfter addition
- customThe product was isolated by distillation
Sources & evidence
- ORD record
- ord-fb49b9fbb5004e5185b6ebca66e3ef01
- Source dataset
- uspto-grants-2004_03
- Patent number
- US06700023B1
Reaction notes
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