Tetrahydrofuran → HCID 86704382, compound

1-Decyne (1.2 g, 6.5 mmol), PdCl2(PPh3)2 (0.12 g, 0.16 mmol), CuI (13 mg, 0.065 mmol), and triethylamine (14 ml, 9.8 mmol) were added to a THF (20 ml) solution of 7-methoxy-2-naphthyltrifluoromethane sulfonate (1.0 g, 3.3 mmol). The solution was mixed at room temperature for 4 hours, and diluted with water (30 ml). The solution was made acidic with diluted hydrochloric acid (2 M), and extracted with dichloromethane (30 ml×3). The extracted solution was washed with water (100 ml×3), and dried with MgSO4. The solution was condensed, and subjected to column chromatography (silica gel, developed with dichloromethane) to obtain 7-decyn-1-yl-2-methoxynaphthalene as a light yellow oil product. The obtained 7-decyn-1-yl-2-methoxynaphthalene (2.8 mmol) and a THF (13 ml) of 10% Pd/C (0.16 g) were placed in a 50 ml round-bottomed flask. Under a hydrogen atmosphere, the solution was stirred until the reaction was completed (approximately 12 hours) while the reaction was tracked using TLC. When the reaction was completed, a catalyst was filtered out, and the filtrate was condensed. The condensed solution was refined by column chromatography (silica gel, developed with dichloromethane) to obtain 7-decyl-2-methoxynaphthalene (compound (3)-12) (0.80 g, 82%).

1. custom(approximately 12 hours)
2. filtrationa catalyst was filtered out
3. customcondensed

ORD record

ord-d180f0df25304752b8507a56910ba185

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018630B2