Tetrahydrofuran → HCID 19363421, compound

HRID 850424Notes

Reaction equation

Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:4][C:3]=1[C:18]([OH:20])=[O:19].O1CCCC1.CCCCCC.C([Li])CCC>[Cl-].[Na+].O.O>[CH2:13]([O:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:2]=[C:3]([C:18]([OH:20])=[O:19])[CH:4]=1)[CH2:14][CH2:15][CH2:16][CH3:17]

Participants

Conditions

Temperature: -78 °C

Procedure

1-Bromo-4-pentyloxynaphthalene-2-carboxylic acid (400 mg, 1.19 mmol) and tetrahydrofuran (THF, 3 ml) were mixed in a reaction vessel replaced with argon, and this solution was cooled to -78° C. A hexane solution (1.6M, 1.63 ml) of n-butyllithium (2.61 mmol) was added, and the mixture was stirred for 1 hour. Water (0.5 ml) and saturated brine (2 ml) were added, and the aqueous layer was extracted 4 times with ethyl acetate (5 ml). The organic layers were combined and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (hexane/ethyl acetate=3/1-1/2) to give 4-pentyloxynaphthalene-2-carboxylic acid (149.6 mg, 49%) as colorless crystals.

Workup

extractionthe aqueous layer was extracted 4 times with ethyl acetate (5 ml)
dry with materialdried over anhydrous magnesium sulfate
filtrationThe drying agent was filtered off
concentrationthe filtrate was concentrated under reduced pressure
customThe obtained residue was purified by column chromatography (hexane/ethyl acetate=3/1-1/2)

Sources & evidence

ORD record: ord-fbe45d71aa474cf9b2747ce5d4cf18e0
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06017919

Reaction notes

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