Acetonitrile → 5-Fluoro-4-(fluoromethyl)-4-methyl-3-oxopentanenitrile
Reaction equation
[F:1][CH2:2][C:3]([CH2:9][F:10])([CH3:8])[C:4](OC)=[O:5].[H-].[Na+].[CH3:13][C:14]#[N:15]>C1COCC1>[F:1][CH2:2][C:3]([CH2:9][F:10])([CH3:8])[C:4](=[O:5])[CH2:13][C:14]#[N:15]Participants
5
Conditions
- Temperature
- 70 °C
Procedure
According to the procedure described in Example 161B Step 1, methyl 3-fluoro-2-(fluoromethyl)-2-methylpropanoate (5.21 g, 34.2 mmol), NaH (1.248 g, 52 mmol), and MeCN (2.791 g, 68 mmol) in THF (40 mL) were heated at 70° C. overnight, to afford 5-fluoro-4-(fluoromethyl)-4-methyl-3-oxopentanenitrile as oil (4.412 g, 80%). 1H NMR (300 MHz, CDCl3) δ 4.67 (m, 2H), 4.52 (m, 2H), 3.80 (s, 2H), 1.27 (s, 3H).
Sources & evidence
- ORD record
- ord-12d7f52be2b548929ed95d3f8aabdf29
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618289B2
Reaction notes
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