Racemate of (3aR,4S,9bR)-4-(p-tolyl)-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline
DOI: 10.14469/hpc/4149 Metadata
Created: 2018-05-10 15:36
Last modified: 2019-02-05 16:48
License: Creative Commons: Public Domain Dedication 1.0
Funding: (none given)
Co-author: Alan Spivey Co-author: Henry Rzepa
Description
To an NMR tube was added ortho-aminobenzaldehye (7.7 mg, 0.06 mmol, 1 equiv) and homoallylic alcohol (14.6 mg, 0.09 mmol, 1.5 equiv). In a separate vial was weighed CSA (13.8 mg, 0.06 mmol, 1 equiv) which was dissolved in HFIP and CDCl3. This was then transferred to the NMR tube to yield a red solution. The reaction was monitored by NMR analysis and quenched after six hours by addition of sat. NaHCO3. The organic layer was extracted with DCM, dried over anhydrous Na2SO4 and concentrated under a stream of N2. The product was isolated by flash column chromatography 25% diethyl ether/petroleum ether.
Files
| Filename | Size | Type | Description |
|---|---|---|---|
| 1H.zip | 368KB | application/zip | Bruker 1H data |
| 1H.mnpub | 0 | chemical/x-mnpub | Mestrenova signature file for 1H.zip |
| 13C.zip | 376KB | application/zip | Bruker 13C data |
| 13C.mnpub | 0 | chemical/x-mnpub | Mestrenova signature file for 13C.zip |
| 1H+13C_NMR.mnova | 467KB | chemical/x-mnova | MestreNova files |
| 1H+13C_NMR.mnpub | 0 | chemical/x-mnpub | Mestrenova signature file for 1H+13C_NMR.mnova |
| cis_NH_aniline.cdxml | 7KB | chemical/x-cdxml | Chemdraw connectivity |
| COSY.zip | 3MB | application/zip | Bruker COSY data |
| COSY.mnpub | 0 | chemical/x-mnpub | Mestrenova signature file for COSY.zip |
| MS.docx | 54KB | application/octet-stream | MS |
| IR.pdf | 9KB | application/pdf | IR |
Member of collection / collaboration
| DOI | Description |
|---|---|
| 10.14469/hpc/3943 | FAIR Data: Reversibility and reactivity in an acid catalyzed cyclocondensation to give furanochromanes , a reaction at the oxonium-Prins vs. ortho-quinone methide cycloaddition mechanistic nexus |
Subject Keywords
| Keyword | Value |
|---|---|
| inchi | InChI=1S/C18H19NO/c1-12-6-8-13(9-7-12)17-15-10-11-20-18(15)14-4-2-3-5-16(14)19-17/h2-9,15,17-19H,10-11H2,1H3/t15-,17-,18+/m1/s1 |
| inchikey | JSZKMJJORLWRAX-NXHRZFHOSA-N |