HuagongsheHuagongshe Chemistry Print Report · For research reference only
Oxalyl chloride → 4-Benzyloxy-2-fluorobutyronitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | Trimethylsilyl cyanide | HCID 82115 | — |
| Reactant | (Diethylamino)sulfur trifluoride | HCID 123472 | — |
| Reactant | 3-(Benzyloxy)propanal | HCID 10888261 | — |
| Catalyst | zinc(II)iodide | HCID 9883512 | — |
| Product | 4-Benzyloxy-2-fluorobutyronitrile | HCID 20149458 | — |
Reaction Steps
The compound 1,3-propanediol 13 is mono-alkylated to yield the 3-benzyloxy-1-propanol, which is then oxidized by means of oxalyl chloride to the corresponding 3-benzyloxy-1-propanal, 15. Reaction with trimethylsilylcyanide, preferably in the presence of a catalytic amount of zinc iodide, followed by treatment with diethylaminosulfurtrifluoride results in the formation of 4-benzyloxy-2-fluorobutyronitrile, 16.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04730006 |
| Source dataset | uspto-grants-1988_03 |
| ORD ID | ord-b6de60400abe4129a15e14c9378f3cba |
| Source note | uspto-grants-1988_03 |