Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 12343242 | HCID 12343242 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66988323 | HCID 66988323 | 44% |
Reaction Steps
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%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08871187B2 |
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| Source dataset | uspto-grants-2014_10 |
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| ORD ID | ord-bd2140d5585843479997509ae4177c34 |
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| Source note | uspto-grants-2014_10 |
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