Hexane → trans-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-ethyl-(3-isopropenylbenzyl)amine

HRID 1356821Notes

Reaction equation

HRID 1356821 reaction equation
[CH2:1]([Li])CCC.CCCCCC.[CH3:12][C:13]([CH3:33])([CH3:32])[C:14]#[C:15]/[CH:16]=[CH:17]/[CH2:18][N:19]([CH2:22][C:23]1[CH:24]=[C:25]([C:29](=O)[CH3:30])[CH:26]=[CH:27][CH:28]=1)[CH2:20][CH3:21]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:12][C:13]([CH3:33])([CH3:32])[C:14]#[C:15]/[CH:16]=[CH:17]/[CH2:18][N:19]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([CH3:1])=[CH2:30])[CH:24]=1)[CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 8058HexaneHCID 18509427trans-3'-[N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-ethylaminomethyl]acetophenoneHCID 178418339Butyllithium

Product 1

HCID 18509410trans-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-ethyl-(3-isopropenylbenzyl)amineYield 73.6%

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

The procedure described in Example 9 was repeated, except that methyl triphenylphosphonium bromide (2.35 g; 6.6 mmol), n-butyl lithium in n-hexane (1.56 M: 4.2 ml; 6.6 mmol), and Compound 43 (1.3 g; 4.4 mmol) were used, to thereby yield 950 mg of the target compound (yield: 73.6%).

Sources & evidence

ORD record
ord-00d3a23a393143218026f73dfbcb4a1e
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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