Hexane → 2-Dipropylamino-8-methylthio-1,2,3,4-tetrahydronaphthalene

HRID 256564Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH2:8][CH2:7]2.C([Li])CCC.CCCCCC.[CH3:30][S:31]SC>O1CCCC1.O>[CH2:13]([N:12]([CH2:16][CH2:17][CH3:18])[CH:9]1[CH2:8][CH2:7][C:6]2[C:11](=[C:2]([S:31][CH3:30])[CH:3]=[CH:4][CH:5]=2)[CH2:10]1)[CH2:14][CH3:15]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 8-bromo-2-di-n-propylamino-1,2,3,4-tetrahydronaphthalene (600 mg, 1.93 mMol) in tetrahydrofuran (20 mL) at -78° C. was added a solution of n-butyllithium in hexane (1.6 M, 1.9 mL, 3.04 mMol). The solution was stirred at -78° C. for one hour, forming a light orange solution. Dimethyl disulfide (0.24 mL, 3.00 mMol) was added, and the reaction mixture was allowed to warm gradually to room temperature. The colorless solution was diluted with water and extracted with dichloromethane. The dichloromethane extracts were combined, dried (Na2SO4), and concentrated in vacuo to give the crude product as a light yellow oil. Purification by flash chromatography (3% methanol in dichloromethane+ tr. NH4OH) gave the product as a colorless, viscous oil (430 mg, 80%). The hydrochloride salt was formed. Recrystallization (ethanol/diethyl ether) gave a colorless, crystalline solid (m.p.=185° C.).

Workup

customforming a light orange solution
temperatureto warm gradually to room temperature
extractionextracted with dichloromethane
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customto give the crude product as a light yellow oil
customPurification by flash chromatography (3% methanol in dichloromethane+ tr. NH4OH)

Sources & evidence

ORD record: ord-38b33c1164ab486990b77e9053ff4e22
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05258379

Reaction notes

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