Methanol → Methyl 8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate

反応式

[O:1]=[C:2]1[C:11]2[CH:10]=[C:9]([C:12]([OH:14])=[O:13])[CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.S(Cl)(Cl)=O.[CH3:19]O>>[O:1]=[C:2]1[C:11]2[CH:10]=[C:9]([C:12]([O:14][CH3:19])=[O:13])[CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1

参加物

反応物 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 147565478-Oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

生成物 1

HCID 10987358Methyl 8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate収率 94%

実験手順

To a solution of 8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid (16 g, 0.084 mol) in MeOH was added thionylchloride (23 g, 0.2 mol). The mixture was then stirred at rt for 12 h. The solvent was removed under vacuum and the residue was taken up in EtOAc (200 ml). The organic layer was washed with a 10% aqueous solution of NaHCO3, dried over MgSO4 and evaporated to give 16 g (94%) of the titled compound as a liquid. TLC: Chloroform/MeOH (9/1), Rf=0.9.