METHYL1-OXO-1,2,3,4-TETRAHYDRONAPHTHALENE-2-CARBOXYLATE

Under nitrogen atmo-sphere, α-tetralone (25.0 mmol, 3.33 mL), dimethyl carbonate (300 mmol, 25.0 mL), sodium hydride (60percent in mineral oil, 50.0 mmol, 2.00 g) and dry methanol (0.1 mL) are heated to 80 °C and stirred for 3 hours. After cooling, hydrochloric acid (3 N, 30.0 mL) is added, the mixture is extracted with ethyl acetate and the combined organic phases are dried over sodium sulphate. After removing the solvent, 4 (5.06 g, 100percent) is obtained as a red-brown liquid.General procedure: A solution of α-tetralone (10 mmol) in dimethyl carbonate(5 mL) was added to a stirred suspension of NaH (60percent dispersion, 15 mmol) in dimethyl carbonate (10 mL) under argon atmosphere.The solution was refluxed and once the reaction was judged completeafter a TLC test the solvent was evaporated. The resultant solid was dissolved in hydrochloric acid (2 M) and the phases were separated. The aqueous phase was extracted with ethyl acetate(35 mL). The organic extracts were dried (MgSO4) and evaporated to dryness. Flash chromatography (EtOAc/hexane 10percent) afforded the pure products. 4.2.1. Methyl 1-oxo-1, 2, 3, 4-tetrahydronaphthalene-2-carboxylate(5a).33 Yield 92percent; brown solid; mp66e68 C; Rf 0.35 (hexane/EtOAc 10/1). IR (KBr) (cm1): 2946; 2897; 1728; 1677; 1598; 1451;1372; 1313; 1156; 949; 900; 732; 1H NMR (CDCl3, 400 MHz) dH:12.41 (s, 1H), 8.04 (d, J7.9 Hz, 1H), 7.78 (d, J7.6 Hz, 1H), 7.47e7.43(m, 1H), 7.30e7.23 (m, 3H), 7.21 (d, J7.6 Hz, 1H), 7.13 (d, J7.1 Hz), 3.79 (s, 3H), 3.75 (s, 3H), 3.59 (dd, J10.5, 4.7 Hz, 1H), 3.04e2.92 (m, 2H), 2.77 (dd, J10.8, 4.6 Hz, 2H), 2.57e2.51 (m, 2H), 2.49e2.42 (m, 1H), 2.34e2.29 (m, 1H); 13C NMR (CDCl3, 100 MHz) dC: 193.3, 173.2, 170.7, 165.2, 143.8, 139.5, 134.0, 131.8, 130.6, 130.0, 128.9, 127.8, 127.5, 127.0, 126.7, 124.4, 96.9, 54.5, 52.5, 51.8, 27.8, 27.7, 26.5, 20.6;MS (EI) m/z (percent): 204 (M), 189, 172, 144, 127, 118, 115, 90, 77, 63, 51.General procedure: A solution of the α-tetralone (10 mmol) in dimethyl carbonate (5 mL) was added to a stirred suspension of NaH (60percent dispersion, 15 mmol) in dimethyl carbonate (10 mL) under an atmosphere of argon. The solution was refluxed; when the reaction was complete (TLC monitoring) the solvent was evaporated. The resultant solid was dissolved in 2 M HCl and the phases were separated. The aqueous phase was extracted with EtOAc (3 × 15 mL). The organic extracts were dried (MgSO4) and evaporated to dryness. Flash chromatography (10percent EtOAc/hexane) afforded the pure products.Preparation of Compound 1; IPrOH Step A - Synthesis of Compound 1 bTo MeMethyl 1-oxo-1, 2, 3, 4-tetrahydronaphthalene-2-carboxylate

Molecular Weight:204.22
XLogP3:2.1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:204.078644241
Monoisotopic Mass:204.078644241
Topological Polar Surface Area:43.4
Heavy Atom Count:15
Complexity:272
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes