2-Bromo-1,4-dimethoxynaphthalene → 2-(1,4-Dimethoxy-3-naphthylcarbonyl)-5-(2-methyldioxolan-2-yl)-6-oxa-bicyclo[3,2,1]octan-7-one

HRID 846864Notes

Reaction equation

HRID 846864 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[C:5](Br)[CH:4]=1.C([Li])CCC.C[O:22][C:23]([CH:25]1[CH2:31][CH2:30][C:29]2([C:33]3([CH3:38])[O:37][CH2:36][CH2:35][O:34]3)[CH2:32][CH:26]1[C:27](=[O:39])[O:28]2)=O>O1CCCC1>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[C:5]([C:23]([CH:25]2[CH2:31][CH2:30][C:29]3([C:33]4([CH3:38])[O:37][CH2:36][CH2:35][O:34]4)[CH2:32][CH:26]2[C:27](=[O:39])[O:28]3)=[O:22])[CH:4]=1

Participants

5

Reactant 3

HCID 117804862-Bromo-1,4-dimethoxynaphthaleneHCID 134534872-Methoxycarbonyl-5-(2-methyldioxolan-2-yl)-6-oxabicyclo[3,2,1]octan-7-oneHCID 178418339Butyllithium

Product 1

HCID 198839072-(1,4-Dimethoxy-3-naphthylcarbonyl)-5-(2-methyldioxolan-2-yl)-6-oxa-bicyclo[3,2,1]octan-7-oneYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Following the method described in Example 4, a solution of 3.2 g of 1,4-dimethoxy-3-bromo-naphthalene in anhydrous tetrahydrofuran was treated at -78° C. with n-butyllithium and then added to a solution in anhydrous tetrahydrofuran of 2.7 g of the compound prepared in Example 3. After silica gel column purification 2.8 g of the title compound was obtained (65% yield) m/z 426 (M+.): IR (film): 1780 cm-1 (C=O, five membered ring lactone), 1670 cm-1 (C=O, benzylic ketone); PMR (CDCl3): inter alia: δ1.4 (s, CH3), 3.85 (s, two OCH3), 3.9 (s, --O--CH2 ----CH2 --O--), 6.9 (s, aromatic H) and 7.4-8.4 (m, four aromatic H).

Workup

  1. customAfter silica gel column purification 2.8 g of the title compound
  2. customwas obtained (65% yield) m/z 426 (M+.)

Sources & evidence

ORD record
ord-710b62f5d51245b9a10df88a8b31f1e0
Source dataset
uspto-grants-1992_08
Patent number
US05138042

Reaction notes

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