Acetonitrile → 5-Fluoro-4-(fluoromethyl)-4-methyl-3-oxopentanenitrile

HRID 871532Notes

Reaction equation

HRID 871532 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

Reactant 3

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 86653519Methyl 3-fluoro-2-(fluoromethyl)-2-methylpropanoate

Product 1

HCID 866535185-Fluoro-4-(fluoromethyl)-4-methyl-3-oxopentanenitrileYield 80.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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-0b79607d11cf4adb819c2d511071d0f0
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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