Hydrochloric Acid → 1-(1,4-Dimethoxy-3-naphthylcarbonyl)-2-methoxycarbonyl-4-acetyl-4-hydroxy-cyclohexane

HRID 846865Notes

Reaction equation

HRID 846865 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]([C:15]([CH:17]2[CH2:23][CH2:22][C:21]3([C:25]4([CH3:30])OCC[O:26]4)[CH2:24][CH:18]2[C:19](=[O:31])[O:20]3)=[O:16])[CH:4]=1.Cl.[CH3:33][OH:34]>>[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:15]([CH:17]2[CH2:23][CH2:22][C:21]([C:25](=[O:26])[CH3:30])([OH:20])[CH2:24][CH:18]2[C:19]([O:34][CH3:33])=[O:31])=[O:16])[CH:4]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 198839072-(1,4-Dimethoxy-3-naphthylcarbonyl)-5-(2-methyldioxolan-2-yl)-6-oxa-bicyclo[3,2,1]octan-7-one

Product 1

HCID 198839141-(1,4-Dimethoxy-3-naphthylcarbonyl)-2-methoxycarbonyl-4-acetyl-4-hydroxy-cyclohexane

Procedure

Operating as described in Example 5, the treatment of 2-(1,4-dimethoxy-3-naphthylcarbonyl)-5-(2-methyldioxolan-2-yl)-6-oxa-bicyclo[3,2,1]octan-7-one, prepared as described in Example 10, with a solution of hydrogen chloride in methanol afforded 1-(1,4-dimethoxy-3-naphthylcarbonyl)-2-methoxycarbonyl-4-acetyl-4-hydroxy-cyclohexane (X, R=H) in almost quantitative yield. m/z 414 (M+.): IR (film): 3460 cm-1 (OH), 1730 cm-1 (C=O ester), 1710 cm-1 (C=O ketone) and 1670 cm-1 (C=O, benzylic ketone). PMR (CDCl3): inter alia: δ2.3 (s, CH3CO), 2.9-3.6 (m, two H), 3.7-3.9 (s, three OCH3), 6.9 (s, aromatic H) and 7.4-8.4 (m, four aromatic H).

Sources & evidence

ORD record
ord-8679de595723454e951bd8c263b6ed65
Source dataset
uspto-grants-1992_08
Patent number
US05138042

Reaction notes

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