3-[5-(Benzyloxy)-1H-indol-1-yl]propanoic acid synthesis
- Product Name:3-[5-(Benzyloxy)-1H-indol-1-yl]propanoic acid
- CAS Number:445492-18-2
- Molecular formula:C18H17NO3
- Molecular Weight:295.33
539-74-2
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1215-59-4
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445492-18-2
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Yield:445492-18-2 49%
Reaction Conditions:
with potassium hydroxide;acetic acid in dimethyl sulfoxide;
Steps:
53.a 4-{5-[2-(5-Methyl-2-phenyl-oxazol-4-yl)-ethoxy]-indol-1-yl}-propionic acid (140a)
3-(5-Benzyloxy-indol-1-yl)-propionic acid (136a). A solution of 5-Benzyloxyindole (4 g, 17.9 mmol) and potassium hydroxide (5.03 g, 89.6 mmol) in DMSO (30 mL) was stirred at room temperature for 1.5 hours. Ethyl 3-bromopropionate (2.75 mL, 21.5 mmol) was added and the mixture stirred for 3 hours. The reaction was diluted with water, acidified with 2N HCl, extracted with ethyl acetate, dried over MgSOs, and concentrated under reduced pressure. The crude oil was chromatographed eluding with 25%-30% EtOAc (with 20% HOAc) in hexanes to yield the desired propionic acid (2.56 g, 49%). 400 MHz 1H NMR (DMSO-d6) δ7.40 (m, 2H), 7.33 (m, 3H), 7.25 (m, 2H), 7.06 (d, 1H, J=2.4 Hz), 6.80 (dd, 1H, J=8.8, 2.4 Hz), 6.24 (dd, 1H, J=2.9, 0.7 Hz), 5.03 (s, 2H), 4.29 (t, 2H, J=6.7 Hz), 2.66 (t, 2H, J=6.7 Hz). MS m/z 324 (M+1).
References:
US2003/171377,2003,A1
1215-59-4
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445492-18-2
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$57.50/250mg