HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → 6-Trimethlsilanylethynyl-2,2,4,4-tetramethyl chroman-8-carbaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 6-Bromo-2,2,4,4-tetramethyl chroman-8-carbaldehyde | HCID 22568946 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 6-Trimethlsilanylethynyl-2,2,4,4-tetramethyl chroman-8-carbaldehyde | HCID 59692081 | 99% |
Reaction Steps
Following general procedure I and using 6-bromo-2,2,4,4-tetramethyl chroman-8-carbaldehyde (Compound 42, see U.S. Pat. No. 6,303,785, 1.78 g, 5.4 mmol), triethyl amine (5 mL), tetrahydrofuran (10 mL), copper(I)iodide (0.23 g, 1.2 mmol), trimethylsilyl acetylene (3.3 mL, 23 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.843 g, 1.2 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 5% ethyl acetate in hexane as the eluent, the title compound (1.77 g, 99%) was obtained as a pale yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07351737B2 |
| Source dataset | uspto-grants-2008_04 |
| ORD ID | ord-a4c16d5fad3e4c2fbd60ff517b05dc2c |
| Source note | uspto-grants-2008_04 |