ChemicalBook CAS DataBase List 8-methoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one

8-methoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one synthesis

6synthesis methods

Product Name:8-methoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one
CAS Number:98232-51-0
Molecular formula:C11H12O3
Molecular Weight:192.21

41214-27-1

98232-51-0

General procedure for the synthesis of 8-methoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one from 3-methoxyphenoxybutyric acid: a chlorobenzene solution of polyphosphoric acid (PPA) was slowly added to compound Int-19d (22 g, 0.1 mol) at 80 °C and the reaction mixture was kept stirred continuously at 80 °C for about 15 hours. After completion of the reaction, the solvent was removed and the residue was dissolved in ethyl acetate and washed sequentially with 1N aqueous sodium hydroxide and saturated saline. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the target compound Int-19e (14 g, 73% yield). The product was characterized by 1H NMR (CDCl3) with chemical shifts δ: 7.74 (d, J = 8Hz, 1H), 6.63 (d, J = 8Hz, 1H), 6.53 (s, 1H), 4.21 (t, J = 12Hz, 2H), 3.80 (s, 3H), 2.84 (t, J = 16Hz, 2H), 2.18-2.15 (m, 2H ).

41214-27-1
6 suppliers
inquiry

98232-51-0
34 suppliers
$45.00/25mg

Yield:98232-51-0 73%

Reaction Conditions:

with PPA in chlorobenzene at 80; for 15 h;

Steps:

19.C

The solution of PPA in chlor-benzene was added Compound Int-19d (22 g, 0.1 mol) at 80 °C and the mixture was allowed to stir at 80 °C for about 15 hours. The solution was removed and the residue was dissolved in ethyl acetate and washed with NaOH (IN, aqueous) followed by brine. The organic layer was dried over Na₂S0₄, filtered and concentrated in vacuo to provide Compound Int-19e (14 g, 73 %). 1H NMR (CDC1₃) 6: 7.74 (d, J= 8 Hz, 1 H), 6.63 (d, J= 8 Hz, 1 H), 6.53 (s, 1 H), 4.21 (t, J= 12 Hz, 2 H), 3.80 (s, 3 H), 2.84 (t, J - 16 Hz, 2 H), 2.18 - 2.15 (m, 2H).

References:

WO2012/50848,2012,A1 Location in patent:Page/Page column 109-110

150-19-6 Synthesis