Trimethylsilyldiazomethane → 4-Fluoro-3-methoxy-4-methylpent-2-enenitrile

HRID 1917883Notes

Reaction equation

HRID 1917883 reaction equation
[F:1][C:2]([CH3:9])([CH3:8])[C:3](=[O:7])[CH2:4][C:5]#[N:6].[CH3:10][Si](C=[N+]=[N-])(C)C>C(OCC)C>[F:1][C:2]([CH3:9])([CH3:8])[C:3]([O:7][CH3:10])=[CH:4][C:5]#[N:6]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 866535074-Fluoro-4-methyl-3-oxopentanenitrile

Product 1

HCID 866535164-Fluoro-3-methoxy-4-methylpent-2-enenitrileYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 4-fluoro-4-methyl-3-oxopentanenitrile (1 g, 7.75 mmol) in dry diethyl ether (150 mL) at 0° C., was added dropwise (trimethylsilyl)diazomethane (4.65 mL of a 2.0 M solution in diethyl ether, 9.30 mmol). After warming to room temperature the reaction mixture was stirred for a further 15 h. The reaction mixture was concentrated under reduced pressure to afford 4-fluoro-3-methoxy-4-methylpent-2-enenitrile as a yellow oil (1 g, 91%) which was taken on to the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 4.89 (s, 1H), 4.23 (s, 3H), 1.47 (d, J=21 Hz, 6H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-786712c9e01c4a62833d5617cbb8dc92
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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