Methyl formate → CID 23682802

HRID 627620Notes

Reaction equation

HRID 627620 reaction equation
[H-].[Na+:2].[CH3:3][O:4][CH:5]([O:9][CH3:10])[CH2:6][C:7]#[N:8].[CH:11](OC)=[O:12]>C(OCC)C>[C:7](/[C:6](/[CH:5]([O:9][CH3:10])[O:4][CH3:3])=[CH:11]\[O-:12])#[N:8].[Na+:2]

Participants

5

Reactant 3

HCID 7865Methyl formateHCID 24758Sodium hydrideHCID 937313,3-Dimethoxypropiononitrile

Product 1

HCID 23682802CID 23682802Yield 46.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of NaH (60% dispersion in mineral oil, 2.52 g, 63.0 mmol) in diethylether (75 mL) was added 3,3-dimethoxypropanenitrile (6.17 mL, 55.0 mmol) followed by methyl formate (6.74 mL, 110 mmol). The solution was stirred for 3 days at RT. The resulting solid was collected by vacuum filtration and washed with ether to afford sodium (E)-2-cyano-3,3-dimethoxyprop-1-en-1-olate (4.2 g, 25.4 mmol).

Workup

  1. filtrationThe resulting solid was collected by vacuum filtration
  2. washwashed with ether

Sources & evidence

ORD record
ord-f2bbf5f441754157bfa1fa669e1873b6
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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