HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisobutylaluminum hydride → (E)-2-Fluoro-3-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-pent-2-en-1-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisobutylaluminum hydride | HCID 14487 | — |
| Reactant | (E)-2-Fluoro-3-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-pent-2-enoic acid ethyl ester | HCID 69725925 | — |
| Reactant | 2-Fluoro-3-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-pent-2-enoic acid ethyl ester | HCID 69725927 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (E)-2-Fluoro-3-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-pent-2-en-1-ol | HCID 69729376 | — |
Reaction Steps
Following General Procedure C and using (E) 2-fluoro-3-(3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-pent-2-enoic acid ethyl ester (Intermediate 15, 3.3 g, 8.4 mmol), CH2Cl2 (50 mL), and DIBAL-H (33.6 mL, 1.0 M in THF, 33.6 mmol) followed by flash column chromatography on silica gel (10%→20% EtOAc-hexane), the title compound was obtained as a white solid (2.4 g, 75% over 2 steps).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06759547B1 |
| Source dataset | uspto-grants-2004_07 |
| ORD ID | ord-3645678dc1ec44568d0403b4dcca922a |
| Source note | uspto-grants-2004_07 |