METHYL 5-BENZYLOXYINDOLE-3-ACETATE synthesis
- Product Name:METHYL 5-BENZYLOXYINDOLE-3-ACETATE
- CAS Number:5599-44-0
- Molecular formula:C18H17NO3
- Molecular Weight:295.33
4382-53-0
83 suppliers
$89.00/0.25/ G
5599-44-0
26 suppliers
$1275.00/1g
Yield:5599-44-0 96%
Reaction Conditions:
with sulfuric acid in methanol; for 3 h;Reflux;
Steps:
1.1 Step 1. Synthesis of methyl 2-(5-(benzyloxy)-1H-indol-3-yl)acetate (C59)
To a solution of 2-(5-benzyloxy-1H-indol-3-yl)acetic acid (10.0 g, 35.6 mmol) in MeOH (50.0 mL, 1.2 mol) was added H2SO4 (2.0 mL, 37.5 mmol). The reaction mixture was heated to reflux and stirred for 3 hours and then cooled to room temperature. The solvent was evaporated under reduced pressure. The residue was dissolved in EtOAc (200 mL) and washed with aqueous saturated NaHCO3 solution. The organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The resulting residue was purified by silica gel chromatography using 10-90% EtOAc/heptanes gradient to afford 10.1 g of product. Methyl 2-(5-benzyloxy-1H-indol- 3-yl)acetate (96%).1H NMR (400 MHz, Chloroform-d) δ 7.98 (s, 1H), 7.51 (ddd, J = 6.8, 1.5, 0.8 Hz, 2H), 7.46 - 7.39 (m, 2H), 7.35 (d, J = 7.3 Hz, 1H), 7.30 - 7.25 (m, 2H), 7.18 (dd, J = 3.9, 2.5 Hz, 2H), 6.98 (dd, J = 8.8, 2.4 Hz, 1H), 5.14 (s, 2H), 3.76(s, 2H), 3.71 (s, 3H). ESI-MS m/z calc.295.12, found 296.09 (M+1)+.
References:
WO2021/203007,2021,A1 Location in patent:Paragraph 00141; 00249
2436-15-9
104 suppliers
$60.00/1g
5599-44-0
26 suppliers
$1275.00/1g
67-56-1
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$9.00/25ml
4382-53-0
83 suppliers
$89.00/0.25/ G
5599-44-0
26 suppliers
$1275.00/1g