HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Diisopropyl Ether
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Chloride | HCID 5234 | — |
| Reactant | Di-tert-butyl dicarbonate | HCID 90495 | — |
| Reactant | 4-[(3-Amino-2-hydroxypropyl)oxy]benzonitrile | HCID 16782739 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Diisopropyl Ether | HCID 7914 | — |
| Product | Tert-butyl 3-(4-cyanophenoxy)-2-hydroxypropylcarbamate | HCID 21867654 | — |
Reaction Steps
A cooled (0° C.) solution of 4-[(3-amino-2-hydroxypropyl)oxy]benzonitrile (from step (ii) above; 44.6 g, 0.23 mol) in THF:H2O (1.5 L of 1:1) was treated with di-tert-butyl dicarbonate (53 g, 0.24 mol). The mixture was stirred at rt overnight, after which NaCl was added and the resulting organic layer separated. The water layer was extracted with ether and the combined organics were dried and concentrated in vacuo. The resulting oil (70 g) was filtered through a plug of silica, and then crystallised from diethyl ether:di-iso-propyl ether to yield 50 g of the sub-title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07351821B2 |
| Source dataset | uspto-grants-2008_04 |
| ORD ID | ord-0c4296f6b7f94704b983ac3545f12ab2 |
| Source note | uspto-grants-2008_04 |