HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2373440Generated: October 25, 2026
Ethyl Acetate → (3,3-Dimethyl-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-ylethynyl)-trimethyl-silane
https://huagongshe.com/reaction/2373440
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Silica | HCID 24261 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 7-iodo-3,3-dimethyl-3,4-dihydro-2H-benzo[b][1,4]dioxepine | HCID 59852691 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Diisopropylamine | HCID 7912 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (3,3-Dimethyl-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-ylethynyl)-trimethyl-silane | HCID 69292324 | — |
Reaction Steps
To a mixture of [PdCl2(PPh3)2] (1.73 g) and copper(I) iodide (845 mg) under Ar is added a degassed solution of 7-iodo-3,3-dimethyl-3,4-dihydro-2H-benzo[b][1,4]dioxepine (7) (15.0 g) in diisopropylamine (225 ml) and THF (225 ml). Trimetylsilylacetylene (7.27 g) is added and the mixture is stirred over night at 57° C. After addition of AcOEt (1 L) and filtration over dicalite, the solution is washed with 1 N aq. HCl sol. (3×1 L) and brine (2×1 L). The organic layer is dried over Na2SO4 and the solvent is evaporated to yield (3,3-dimethyl-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-ylethynyl)-trimethyl-silane (6b) as a brown oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07459480B2 |
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| Source dataset | uspto-grants-2008_12 |
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| ORD ID | ord-d312b09f768c4ec68baffca2a05e9d02 |
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| Source note | uspto-grants-2008_12 |
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