Hexane → 2-(1,4,5-Trimethoxy-3-naphthylcarbonyl)-5-(2-methyl-dioxolan-2-yl)-6-oxa-bicyclo[3,2,1]octan-7-one
Reaction equation
[CH3:1][CH2:2][CH2:3]CCC.[CH2:7]([Li])CCC.CO[C:14]([CH:16]1[CH2:22][CH2:21][C:20]2([C:24]3([CH3:29])[O:28][CH2:27][CH2:26][O:25]3)[CH2:23][CH:17]1[C:18](=[O:30])[O:19]2)=[O:15].[CH3:31][O:32][CH:33]1[C:39](=[C:40]=[O:41])[CH2:38][C:37]2(C3(C)OCCO3)[CH2:42][CH:34]1[C:35](=O)[O:36]2>O1CCCC1>[CH3:35][O:36][C:37]1[C:38]2[C:39](=[C:40]([O:41][CH3:7])[CH:1]=[CH:2][CH:3]=2)[C:33]([O:32][CH3:31])=[C:34]([C:14]([CH:16]2[CH2:22][CH2:21][C:20]3([C:24]4([CH3:29])[O:25][CH2:26][CH2:27][O:28]4)[CH2:23][CH:17]2[C:18](=[O:30])[O:19]3)=[O:15])[CH:42]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
7 ml of a 1.65 M hexane solution of n-butyllithium was dissolved in 30 ml of anhydrous tetrahydrofuran. To the solution was added at -78° C a solution of 3.3 g of 1,4,5-trimethoxy-3-bromo-naphthalene (VI, R=OCH3) in 30 ml of anhydrous tetrahydrofuran. 2,5 g of 2-methoxy-carbonyl-5-(2-methyl-dioxolan-2-yl)-6-oxa -bicyclo[3,2,1]-octan-7-one, prepared as described in Example 3, was dissolved in 50 ml of anhydrous tetrahydrofuran and added to the reaction mixture. The reaction mixture was stood for 1 hour at -78° C and then quenched with acetic acid. The solvent was removed in vacuo. The residue was purified by silica gel column chromatograhy, giving 3 g (73% yield) of the title compound. m/z 456 (M+.).
Workup
- additionadded to the reaction mixture
- customquenched with acetic acid
- customThe solvent was removed in vacuo
- customThe residue was purified by silica gel column chromatograhy
Sources & evidence
- ORD record
- ord-5b14eb8ac7c3405285f0dddb77d8773f
- Source dataset
- uspto-grants-1990_07
- Patent number
- US04939282
Reaction notes
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