HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Iodophenol → 4-(2-Iodophenoxymethyl)-1-methyl-1,2,3,6-tetrahydropyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Iodophenol | HCID 10784 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 1,2,3,6-Tetrahydro-1-methylpyridine-4-methanol | HCID 118921 | — |
| Reactant | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 4-(2-Iodophenoxymethyl)-1-methyl-1,2,3,6-tetrahydropyridine | HCID 10735093 | 66.4% |
Reaction Steps
4-(Hydroxymethyl)-1-methyl-1,2,3,6-tetrahydropyridine (D1, 5.63 g, 0.044 mol), 2-iodophenol (7.80 g, 0.035 mol) and triphenylphosphine (11.61 g, 0.044 mol) were stirred in dry THF (200 ml) under Ar as diethyl azodicarboxylate (7.0 ml, 0.044 mol) was added portionwise. The solution was stirred for 1 h, concentrated, diluted with ethyl acetate, and extracted with dil. HCl. The extract was basified (sat. K2CO3 solution) and extracted with ethyl acetate. This organic extract was dried (Na2SO4) and evaporated to give a brown oil. Purification by chromatography on silica gel, eluting with 0-10% methanol/chloroform (gradient) gave the title compound (7.65 g, 65%) as an amber oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05972951 |
| Source dataset | uspto-grants-1999_10 |
| ORD ID | ord-ec64b1cbb0c74ae58332e6548c22bf09 |
| Source note | uspto-grants-1999_10 |