Diethyl Ether → Benzenemethanamine, N-[3-methyl-1-(2-propenyl)-2-butenyl]-

HRID 1596814Notes

Reaction equation

HRID 1596814 reaction equation
[C:1](C(O)(CC=C)C(C)(C)C)(C)([CH3:3])[CH3:2].C([Li])CCC.[CH2:19]([N:26]=[CH:27][CH:28]=[C:29]([CH3:31])[CH3:30])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(OCC)C>CCCCC.[Cl-].[Cl-].[Zn+2]>[CH2:3]([CH:27]([NH:26][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:28]=[C:29]([CH3:31])[CH3:30])[CH:1]=[CH2:2]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 11789696HCID 11789696, compoundHCID 117899023-tert-butyl-2,2-dimethylhex-5-en-3-olHCID 178418339Butyllithium

Product 1

HCID 11085196Benzenemethanamine, N-[3-methyl-1-(2-propenyl)-2-butenyl]-

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8003PentaneSolvent

Procedure

The reaction was performed analogous to Example 1 with 500 mg (2.71 mmol) 3-tert-butyl-2,2-dimethylhex-5-en-3-ol, 1.93 ml (2.71 mmol) of a 1.4-molar n-butyllithium solution in pentane, 468 mg (2.71 mmol) benzyl-(3-methyl-but-2-enylidene)amine and 370 mg (2.71 mmol) ZnCl2. The raw product obtained was cleaned by means of a silica column with 25-100% diethyl ether/light gasoline. There was obtained the amine as a colorless oil.

Workup

  1. customThe raw product obtained

Sources & evidence

ORD record
ord-c23c5a794e214b319f3c731f9bc0550f
Source dataset
uspto-grants-2001_09
Patent number
US06291713B1

Reaction notes

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