Sodium Hydroxide → N-ethyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine

HRID 1759788Notes

Reaction equation

[CH3:1][C:2]1([CH3:18])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([NH:14][C:15](=O)[CH3:16])[CH:5]=[CH:4][C:3]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.O>[CH2:15]([NH:14][C:6]1[CH:5]=[CH:4][C:3]2[C:2]([CH3:18])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]=2[CH:7]=1)[CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide (1.5 g, 6.1 mmole) in 8 mL THF was treated with 2.5 mL of lithium aluminium hydride solution (1M in THF). The reaction mixture was heated to reflux for 3.5 hours. The mixture was cooled to 0° C. and treated with 0.95 mL water, 0.95 mL 15% aqueous sodium hydroxide solution and 3.0 mL water. The mixture was stirred at room temperature until a white precipitate formed. MgSO4 was added, the mixture was filtered and concentrated in vacuo, giving a pale yellow oil. The product was purified by flash chromatography (SiO2, 15% ethyl acetate/hexanes), yielding 1.2 g (86%) of N-ethyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine, as a colourless oil.

Workup

temperatureThe reaction mixture was heated
temperatureto reflux for 3.5 hours
customformed
filtrationthe mixture was filtered
concentrationconcentrated in vacuo
customgiving a pale yellow oil
customThe product was purified by flash chromatography (SiO2, 15% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-2642d9bd9a0f48878c093f590e2ab53a
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06838472B2

Reaction notes

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