HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 2-[5-(4-Cyanophenyl)-2,3-dihydro-1-benzofuran-2-yl]ethyl methanesulfonate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | 4-[2-(2-Hydroxyethyl)-2,3-dihydro-1-benzofuran-5-yl]benzonitrile | HCID 22274597 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-[5-(4-Cyanophenyl)-2,3-dihydro-1-benzofuran-2-yl]ethyl methanesulfonate | HCID 22274466 | 93.1% |
Reaction Steps
To a solution of Example 67C (0.23 g, 0.87 mmol) and methanesulfonyl chloride (0.075 mL, 0.96 mmol) in CH2Cl2 (5 mL) at 0° C. was added triethylamine (0.13 mL, 9.4 mmol). The mixture was stirred for 30 minutes, diluted with CH2Cl2 (75 mL), washed with water (3×100 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified on silica using CH2Cl2 to provide the titled compound (0.278 g, 90%). 1HNMR (CDCl3): H NMR: 1.95 (m, 2H), 2.93 (m, 2H), 3.00 (s, 3H), 3.46 (m, 2H), 5.00 (m, 1H), 6.81 (d, J=7 Hz, 1H), 7.40 (m, 2H), 7.65 (m, 4H); MS (DCI) 343 (M+), 361 (M+NH4+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07538138B2 |
| Source dataset | uspto-grants-2009_05 |
| ORD ID | ord-65026d9b6f5643fcb8d38d88ea9405c2 |
| Source note | uspto-grants-2009_05 |