Tetrahydrofuran → 2-Decyl-6-methoxynaphthalene

A THF solution of n-decyl magnesium bromide (prepared as a THF (2 ml) solution of n-decyl bromide (2.2 ml, 11 mmol) and Mg (292 mg, 12 mmol)) was added to 6-bromo-2-methoxynaphthalene (2.37 g, 10 mmol) easily available from a reagent manufacturer and a THF (10 ml) solution of Ni(dppp)Cl2 (271 mg, 0.5 mmol), and the mixture was heated under reflux for 19 hours. After cooling, the mixed solution was diluted with water (10 ml), and non-reacted Mg was filtered out. The filtered solution was extracted with ether (5 ml×3). The extracted organic phases were collected (10 ml×3), and dried with MgSO4, and condensed with an evaporator. The condensed organic phase was recrystallized with hexane to obtain 6-n-decyl-2-methoxynaphthalene (compound (3)-64) as a light yellow solid.

1. temperatureunder reflux for 19 hours
2. temperatureAfter cooling
3. filtrationwas filtered out
4. extractionThe filtered solution was extracted with ether (5 ml×3)
5. customThe extracted organic phases were collected (10 ml×3)
6. dry with materialdried with MgSO4, and condensed with an evaporator
7. customThe condensed organic phase was recrystallized with hexane

ORD record

ord-0a539def97724f5f858adcdbbc2c0a6c

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018630B2