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

HRID 1356790Notes

Reaction equation

HRID 1356790 reaction equation
[CH2:1]([Li])CCC.CCCCCC.[CH:12]1([N:15]([CH2:25][C:26]2[CH:27]=[C:28]([C:32](=O)[CH3:33])[CH:29]=[CH:30][CH:31]=2)[CH2:16]/[CH:17]=[CH:18]/[C:19]#[C:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:14][CH2:13]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:12]1([N:15]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([CH3:33])=[CH2:1])[CH:27]=2)[CH2:16]/[CH:17]=[CH:18]/[C:19]#[C:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 8058HexaneHCID 18509435trans-3'-[N-Cyclopropyl-N-(6,6-dimethyl-2-hepten-4-ynyl)aminomethyl]acetophenoneHCID 178418339Butyllithium

Product 1

HCID 18509418trans-N-Cyclopropyl-N-(6,6-dimethyl-2-hepten-4-ynyl)-(3-isopropenylbenzyl)amineYield 45.6%

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

The procedure described in Example 9 was repeated, except that methyl triphenylphosphonium bromide (0.57 g; 1.61 mmol), n-butyl lithium in n-hexane (1.56 M: 1.0 ml; 1.61 mmol), and Compound 13 (0.33 g; 1.07 mmol) were used, to thereby yield 0.15 g of the target compound (yield: 45.6%).

Sources & evidence

ORD record
ord-b2a0caa7192040fc8bbd41f34ac8cf34
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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