Chlorotrimethylsilane → Homoveratrylamine

HRID 1843924Notes

Reaction equation

HRID 1843924 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][N+:11]([O-])=O)=[CH:5][C:4]=1[O:14][CH3:15].[Li+].[BH4-].Cl[Si](C)(C)C>C1COCC1>[CH3:15][O:14][C:4]1[CH:5]=[C:6]([CH2:9][CH2:10][NH2:11])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 2220933,4-Dimethoxy-beta-nitrostyreneHCID 4148881Lithium borohydride

Product 1

HCID 8421HomoveratrylamineYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using the same procedure and workup as described in Example 15, 1,2-dimethoxy-4-(2-nitro-vinyl)-benzene (I-40a: 4 g, 19.13 mmol) in dry THF (66 mL) was reacted with LiBH4 (1.6 g, 76.55 mmol) and chloro trimethyl silane (19.3 mL, 152.6 mmol) at 0° C., The resulting mixture was stirred at room temperature for 72 hours to afford 3.46 g of the product (100% yield).

Sources & evidence

ORD record
ord-7e3da1703fc14b26b509ab38c274f1a0
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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