HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2047198Generated: October 26, 2026
Dichloromethane → 4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole
https://huagongshe.com/reaction/2047198
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 8-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-dioxaspiro(4.5)dec-7-ene | HCID 3697076 | — |
| Reactant | 4-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole | HCID 15640871 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole | HCID 66733509 | 57% |
Reaction Steps
To a 10-20 mL microwave vessel was charged 4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole (0.60 mmol, 166 mg), 4,4,5,5-tetramethyl-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane (0.84 mmol, 224 mg), K3PO4 (1.80 mmol, 382 mg), PdCl2(dppf).CH2Cl2 (0.06 mmol, 50 mg) and 9:1 Dioxane:H2O (15 mL). The suspension was sonicated to break up salts, flushed with argon, sealed, and heated to 160° C. for 45 minutes in microwave synthesizer. The reaction was concentrated in vacuo, and the residue purified via silica gel chromatography (0% to 60% ethyl acetate in hexanes) to yield 4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole (115 mg, 0.34 mmol, 57% yield) as clear oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08591943B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-c488b369631e46db9e313390a4f88f82 |
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| Source note | uspto-grants-2013_11 |
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