Trimethylsilyldiazomethane → Methyl 4-hydroxy-1,2,3,4-tetrahydronaphthalene-1-carboxylate

4-Oxo-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (3.50 g, 18.4 mmol) in THF (18.4 ml) was added to a dry flask and the solution was purged and then evacuated with argon. Sodium borohydride (1.74 g, 46.0 mmol) was added in one portion and the mixture was stirred at room temperature overnight. The reaction was diluted with aqueous HCl and the mixture was extracted with EtOAc (3×). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting oily solid was taken-up in methanol/dichloromethane (1:1, 20 ml). Trimethylsilyldiazomethane (18.4 ml, 36.8 mmol) was added drop wise until the solution turned bright yellow and then the mixture was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0 to 100% EtOAc/hexanes) to afford methyl 4-hydroxy-1,2,3,4-tetrahydronaphthalene-1-carboxylate as a yellow oil.

1. customthe solution was purged
2. customevacuated with argon
3. extractionthe mixture was extracted with EtOAc (3×)
4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. concentrationthe mixture was concentrated under reduced pressure
7. customThe residue was purified by column chromatography on silica gel (0 to 100% EtOAc/hexanes)

ORD-Eintrag

ord-46e26952e9334ed68206e7395ef5c6b0

Quelldatensatz

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09242984B2