Aluminium lithium hydride → 2-[4-(Tert-butyldimethylsilanyloxy)-3,5-dimethylphenyl]ethylamine

HRID 6733Notes

Reaction equation

[C:1]([Si:5]([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH:16]=[CH:17][N+:18]([O-])=O)=[CH:11][C:10]=1[CH3:21])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[Si:5]([O:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH2:16][CH2:17][NH2:18])=[CH:11][C:10]=1[CH3:21])([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:6])[CH3:7]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of tert-butyl-[2,6-dimethyl-4-(2-nitrovinyl)phenoxy]dimethylsilane (0.20 g) in 15 mL diethyl ether was cooled to 0° C. Lithium aluminum hydride (0.20 g) was added in portions to the stirring nitroalkene solution. The resulting slurry was refluxed for 3 h and then cooled to 0° C. The mixture is carefully quenched by the sequential addition of 0.2 mL of water, followed by 0.2 mL of 3 N sodium hydroxide and 0.6 mL of water. The mixture was stirred for 15 min, then filtered to remove the aluminum salts. The filtrate was collected and the volatile material was removed by a rotary evaporator to give 100 mg of 2-[4-(tert-butyldimethylsilanyloxy)-3,5-dimethylphenyl]ethylamine.

Workup

temperatureThe resulting slurry was refluxed for 3 h
customThe mixture is carefully quenched by the sequential addition of 0.2 mL of water
filtrationfiltered
customto remove the aluminum salts
customThe filtrate was collected
customthe volatile material was removed by a rotary evaporator

Sources & evidence

ORD record: ord-6430fc8d554d40e2b51cd9ef7a03c206
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084154B2

Reaction notes

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