HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Triethylamine → [4-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyloxy]-acetic acid tert-butyl ester
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | 4,4,5,5-Tetramethyl[1,3,2]dioxaborolane | HCID 2734768 | — |
| Edukt | (3-Iodo-4-methyl-benzyloxy)-acetic acid tert-butyl ester | HCID 69586267 | — |
| Katalysator | HCID 178418476 | HCID 178418476 | — |
| Lösungsmittel | 1,4-Dioxane | HCID 31275 | — |
| Produkt | [4-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyloxy]-acetic acid tert-butyl ester | HCID 69586766 | — |
Reaktionsschritte
The procedure used in Example 3: step b was followed using (3-iodo-4-methyl-benzyloxy)-acetic acid tert-butyl ester ((Example 300: step a) 600 mg, 1.65 mmol), PdCl2(PPh3)2 (58 mg, 0.08 mmol), triethylamine (1.25 mL, 9.4 mmol), and 4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (0.91 mL, 6.4 mmol) in dioxane (5 mL). Analogous aqueous workup and purification by SiO2 flash column chromatography yielded the title compound contaminated with the product resulting from halide reduction (569 mg, 95%). The material was used without further purification. 1H-NMR (CDCl3): δ 7.73 (d, 1H, J=1.9 Hz), 7.38 (dd, 1H, J=2.1, 7.9 Hz), 7.18 (d, 1H, J=7.9 Hz), 4.61 (s, 2H), 3.97 (s, 2H), 2.55 (s, 3H), 1.50 (s, 9H), 1.37 (s, 9H).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US07109354B2 |
| Quelldatensatz | uspto-grants-2006_09 |
| ORD ID | ord-e09c820912814451a06150a1c837e164 |
| Quellennotiz | uspto-grants-2006_09 |