2-(1-Oxo-2,3-dihydro-1H-inden-5-yl)acetic acid synthesis

6synthesis methods

Product Name:2-(1-Oxo-2,3-dihydro-1H-inden-5-yl)acetic acid
CAS Number:125564-43-4
Molecular formula:C11H10O3
Molecular Weight:190.2

1H-Indene-5-acetic acid, 2,3-dihydro-1-oxo-, methyl ester

1391303-26-6
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2-(1-Oxo-2,3-dihydro-1H-inden-5-yl)acetic acid

125564-43-4
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Yield:125564-43-4 87%

Reaction Conditions:

with methanol;sodium hydroxide at 20; for 1 h;

Steps:

1a.2 Step 2

methyl 2-(1 -oxo-2,3-dihydro-1 H-inden-5-yl)acetate Ex.29a (360 mg, 1.76 mmol) was dissolved in MeOH (10 mL)and 2N NaOH (1.06 mL, 2.12 mmol) was added to the solution. The reaction mixture was stirred at rt for 1 h. The solvents were removed under reduced pressure. Et20 and water was added to the residue. The two phases were partitionated. The aqueous layer wasacidified with 1 N citric acid until pH=5 was reached and then extracted with EtOAc. The combined organic layers were dried over Mg504, filtered and the solution was concentrated to dryness to give 2-(1-oxo-2,3-dihydro-1 H-inden-5- yl)acetic acid (290 mg, 87%) as white solid.1 H NMR (300 MHz, DMSO-d6, d in ppm): 2.60 (t, 2H, J=5.8Hz), 3.07 (t, 2H, J=6.OHz), 3.70 (s, 2H), 7.30 (d, 1H, J=7.9Hz), 7.45 (s, 1H), 7.57 (d, 1H,J=7.8Hz), 12.42 (br(s), 1H).

References:

WO2018/138362,2018,A1 Location in patent:Page/Page column 68; 81