Formaldehyde → HCID 66988323, compound

HRID 540392Notes

Reaction equation

HRID 540392 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:9]#[N:10])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:18]=[O:19]>CN(C=O)C>[OH:19][CH2:18][C:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:9]#[N:10]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 24758Sodium hydrideHCID 12343242HCID 12343242, compound

Product 1

HCID 66988323HCID 66988323, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

The crude (4-fluorophenyl)heptanenitrile obtained in stage 9-1-1 is added to a suspension of 1.62 g of 60% NaH in 50 ml of DMF cooled to 0° C. After stirring for 30 minutes, 8.9 g (296 mmol) of paraformaldehyde are added portionwise. The reaction medium is left to stir at ambient temperature for 3 hours and then hydrolysed with ice and extracted with dichloromethane. The organic phase is dried over sodium sulphate, filtered and evaporated under pressure. The crude product obtained is purified by silica gel chromatography (eluent 8/2 heptane/ethyl acetate). 3.85 g in the form of a pale yellow oil are obtained with a yield of 44%.

Workup

  1. waitThe reaction medium is left
  2. stirringto stir at ambient temperature for 3 hours
  3. extractionhydrolysed with ice and extracted with dichloromethane
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated under pressure

Sources & evidence

ORD record
ord-bd2140d5585843479997509ae4177c34
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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