Sodium Hydroxide → HCID 22600030, compound

HRID 1759776Notes

Reaction equation

[CH2:1]([O:3][CH2:4][C:5]([NH:7][C:8]1[CH:17]=[CH:16][C:15]2[C:14]([CH3:19])([CH3:18])[CH2:13][CH2:12][C:11]([CH3:21])([CH3:20])[C:10]=2[CH:9]=1)=O)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>CCOCC.O>[CH2:1]([O:3][CH2:4][CH2:5][NH:7][C:8]1[CH:17]=[CH:16][C:15]2[C:14]([CH3:19])([CH3:18])[CH2:13][CH2:12][C:11]([CH3:20])([CH3:21])[C:10]=2[CH:9]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-ethoxy-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide (35) (674 mg, 2.33 mmole) in 20 mL ether was treated with 400 mg of lithium aluminium hydride and heated at reflux for 3.5 hours. The reaction mixture was cooled to 0° C., treated successively with 0.4 mL water, 0.4 mL 15% aqueous sodium hydroxide solution, 1.2 mL water and stirred at room temperature until a white precipitate formed. MgSO4 was added and the mixture was filtered and concentrated in vacuo to give a pale brown oil. The product was purified by flash chromatography (SiO2, 10% ethyl acetate/hexanes), to yield 484 mg (75%) of (2-ethoxy-ethyl)-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine (37), as a pale yellow oil.

Workup

temperatureheated
temperatureat reflux for 3.5 hours
customformed
filtrationthe mixture was filtered
concentrationconcentrated in vacuo
customto give a pale brown oil
customThe product was purified by flash chromatography (SiO2, 10% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-e0c70854eed3417d8f1c668bd4ac8608
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06838472B2

Reaction notes

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