Sodium Chloride → Butyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine

HRID 1760828Notes

Reaction equation

[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([NH2:14])[CH:5]=[CH:4][C:3]1=2.[CH2:16]([Li])[CH2:17][CH2:18][CH3:19].ICCCC.[Cl-].[Na+]>O1CCCC1>[CH2:16]([NH:14][C:6]1[CH:5]=[CH:4][C:3]2[C:2]([CH3:15])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=2[CH:7]=1)[CH2:17][CH2:18][CH3:19]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-ylamine (1) (0.3 g, 1.5 mmole) in 30 mL tetrahydrofuran (THF) was cooled to −78° C. and 2.5 M n-butyllithium solution (0.6 mL) was added dropwise. The reaction mixture was allowed to warm to 0° C. over a one hour period. Iodobutane (0.171 mL) was added at 0° C. and the reaction mixture was stirred at room temperature for 15 hours. The reaction mixture was then poured into 50 mL of a saturated aqueous sodium chloride solution and extracted with three portions of 50 mL of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to provide a brown oil. The product was purified by flash chromatography (SiO2, 5% ethyl acetate/hexanes) to provide 143 mg (37%) of butyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine (7) as a pale yellow oil.

Workup

extractionextracted with three portions of 50 mL of ethyl acetate
dry with materialThe combined organic extracts were dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customto provide a brown oil
customThe product was purified by flash chromatography (SiO2, 5% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-a962307d7632400794896d4fea996b71
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06844466B2

Reaction notes

Loading…