HuagongsheHuagongshe Chemistry Print Report · For research reference only
Butanoic acid, 4-chloro-, 1,1-dimethylethyl ester → 3-[(tert-Butyl)oxycarbonyl]propyl phenylmethyl butane-1,4-dioate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Butanoic acid, 4-chloro-, 1,1-dimethylethyl ester | HCID 527695 | — |
| Reactant | Cesium monobenzylsuccinate | HCID 86600772 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-[(tert-Butyl)oxycarbonyl]propyl phenylmethyl butane-1,4-dioate | HCID 59730696 | 14.3% |
Reaction Steps
A solution of tert-butyl 4-chlorobutyrate (8.9 g, 50 mmol) and cesium monobenzylsuccinate (prepared from monobenzyl succinate and CsOH) (50 mmol) in 100 mL of DMF was heated at 80° C. for 2 days. DMF was evaporated and chromatographed on silica (hexane-ethyl acetate) to afford 2.5 g (14%) of the title compound 3 as a colorless liquid. 1H NMR (DMSO-d6) δ 7.35 (s, 5H), 5.09 (s, 2H), 3.99 (t, J=7 Hz, 2H), 2.58 (m, 4H), 2.25 (t, J=7 Hz, 2H), 1.93 (q, 2H), 1.41 (s, 9H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07381818B2 |
| Source dataset | uspto-grants-2008_06 |
| ORD ID | ord-af1e4825cede4c4e89a35d132e5d952e |
| Source note | uspto-grants-2008_06 |