ChemicalBook CAS DataBase List 3-acetyl-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one

3-acetyl-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one synthesis

6synthesis methods

Product Name:3-acetyl-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one
CAS Number:1438383-92-6
Molecular formula:C19H16O3
Molecular Weight:292.33

5H-Benzo[d]naphtho[2,3-b]pyran-8(9H)-one, 10,11-dihydro-3-[2-(trimethylsilyl)ethynyl]-

1438383-91-5
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3-acetyl-10,11-dihydro-5H-dibenzo[c,g]chromen-8(9H)-one

1438383-92-6
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Yield:1438383-92-6 86%

Reaction Conditions:

with formic acid at 65; for 3 h;

Steps:

PY-3 3-acetyl-l 0,1 l-dihydro-5H-dibenzo [c,g] chromen-8(9H)-one

A 20 mL vial with stir bar was charged with 3-((trimethylsilyl)ethynyl)-10, l 1 -dihydro-5H- dibenzo[c,g]chromen-8(9H)-one (850 mg, 2.44 mmol) and formic acid (9.8 mL). The solution was heated to 65 °C. After 3 h, the reaction was judged complete. The mixture was concentrated under reduced pressure; the resulting residue was taken up in CH₂CI₂ and loaded onto a prepacked 25g silica gel cartridge. The product was purified by chromatography on a prepacked 80g silica gel column eluting with a solvent gradient from 5% to 85% EtOAc/hexanes. The product containing fractions were combined and concentrated to provide 3-acetyl-l 0, 1 l -dihydro-5H-dibenzo[c,g]chromen-8(9H)- one (616 mg, 86%): 400 MHz ^lH NMR (CDC1₃) δ 8.00 - 7.94 (m, 1H), 7.81 (d, J = 8.2 Hz, 1H), 7.77 (s, 1H), 7.64 (s, 2H), 5.16 (s, 2H), 2.98 (t, J = 6.1 Hz, 2H), 2.69 - 2.64 (m, 2H), 2.63 (s, 3H), 2.21 - 2.09 (m, 2H).

References:

WO2013/75029,2013,A1 Location in patent:Page/Page column 209; 210