HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → HCID 178482623, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Boron trifluoride etherate | HCID 8000 | — |
| Reactant | cyclopenta-1,3-diene;N,N-dimethylcyclopenta-2,4-dien-1-amine;iron(2+) | HCID 129678476 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 178482623 | HCID 178482623 | 76% |
Reaction Steps
A solution of 11 (100 mg, 0.44 mmol) in THF (5 mL) was sequentially treated with BF3.OEt2 (58 μL, 0.46 mmol), n-BuLi (0.51 mL, 1.70 M, 0.87 mmol) and DMF (0.17 mL, 2.18 mmol). Standard workup followed by gradient column chromatography (silica gel, 94:5:1 hexanes/Et2O/Et3N, then 84:15:1 hexanes/Et2O/Et3N) gave 12d (85 mg, 76%) as a red-orange oil; IR (KBr, neat) vmax 3097, 2943, 2851, 2826, 2785, 1667 cm−1, 1H NMR (300 MHz, CDCl3) 10.13 (s, 1H), 4.61 (m, 1H), 4.40 (t, 1H, J=2.7 Hz), 4.29 (m, 1H), 4.27 (s, 5H), 2.70 (s, 6H) ppm; 13C NMR (75.5 MHz, CDCl3) 192.8, 117.5, 71.8, 69.5, 67.7, 66.2, 60.2, 45.6 ppm; EIMS [m/z (%)] 257 (M+, 100), 229 (13), 119 (54), 44 (66); HRMS (EI) calcd for C13H15NO56Fe: 257.0503. Found 257.0504.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07982064B2 |
| Source dataset | uspto-grants-2011_07 |
| ORD ID | ord-aaba26ea110e4d1abc96ebbf57443f6d |
| Source note | uspto-grants-2011_07 |