HuagongsheHuagongshe Chemistry Print Report · For research reference only
Chlorotrimethylsilane → HCID 178482627, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Chlorotrimethylsilane | HCID 6397 | — |
| 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 178482627 | HCID 178482627 | 93% |
Reaction Steps
A solution of 11 (229 mg, 1.0 mmol) in THF (10 mL) was sequentially treated with BF3.OEt2 (0.13 mL, 1.05 mmol), n-BuLi (0.48 mL, 2.30 M, 1.10 mmol) and TMSCl (0.15 mL, 1.20 mmol). Standard workup followed by column chromatography (silica gel, 7:3 hexanes/Et2O, Rf=0.68) gave 12a (279 mg, 93%) as an orange oil; IR (KBr, neat) max 3096, 2952, 2818, 2774, 1247 cm−1; 1H NMR (300 MHz, CDCl3) 4.16 (s, 5H), 4.13 (t, 1H, J=2.7 Hz), 4.10 (m, 1H), 3.86 (m, 1H), 2.57 (s, 6H), 0.33 (s, 9H) ppm; 13C NMR (75.5 MHz, CDCl3) 120.1, 70.6, 68.5, 66.2, 65.9, 58.0, 46.1, 0.5 ppm; EIMS [m/z(%)] 301 (M+, 100); HRMS (EI) calcd for C15H23N28Si56Fe: 301.0949. Found 301.0945.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07982064B2 |
| Source dataset | uspto-grants-2011_07 |
| ORD ID | ord-7a8a18d48dd047d6bf3d465d00626df9 |
| Source note | uspto-grants-2011_07 |