7-DIETHYLAMINO-3-HYDROXYMETHYL-4-METHYL-CHROMEN-2-ONE synthesis
- Product Name:7-DIETHYLAMINO-3-HYDROXYMETHYL-4-METHYL-CHROMEN-2-ONE
- CAS Number:127321-51-1
- Molecular formula:C15H19NO3
- Molecular Weight:261.32
92295-93-7
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27490-33-1
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127321-51-1
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Yield:127321-51-1 35%
Reaction Conditions:
with tetrakis(triphenylphosphine) palladium(0) in 1,4-dioxane at 100 - 120; for 22 h;Sealed tube;
Steps:
7-(diethylainino)-3-(hydroxymetfayI)-4-methyl-2H-chromen-2-one (Int 2-3).
A mixture of Int 2-1 (3 g, 9.67 mmol, 1 eq), tributylstannylmethanol (4.04 g, 12.6 mmol, 1.3 eq) and PdfPPhs)* (559 mg, 484 miho, 0.05 eq) in dioxane (30 mL) was bubbled with nitrogen and vial was sealed. The mixture was stirred at 100 °C for 16 hours and then 120 °C for 6 hours. The mixture was purified by column chromatography over silica gel (petroleum ether/ethyl acetate 10/1 to 1/1). The desired fractions were collected and concentrated under vacuum to give Int 2-3 (924 mg, 3.39 mmol, 35% yield, 96% purity) as a yellow solid. LC-MS [ESI, M+l]: 262. *H NMR (400 MHz, CDCh) d = 7.45 (d, J=9.2 Hz, 1H), 6.62 (dd, J=2.8, 9.2 Hz, 1H) 6.50 (d, J=2.8, 1H), 4.67 (d, J=6.8, 1H), 3.42 (q, 1=1.2, 4H), 2.97 (t, J=6.8, 1H), 2.42 (s, 1H), 1.22 (q, J=7.2, 4H).
References:
WO2020/205683,2020,A1 Location in patent:Paragraph 00122; 00125
91-44-1
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127321-51-1
13 suppliers
$45.00/2.5mg