Ethyl Acetate → Butyl 1-oxoindane-5-carboxylate

HRID 1717690Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.CCN([CH:18]([CH3:20])[CH3:19])C(C)C.C[CH2:22][O:23][C:24](C)=[O:25]>CCCCO.CCCCCC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[O:11]=[C:7]1[C:8]2[C:4](=[CH:3][C:2]([C:24]([O:23][CH2:22][CH2:20][CH2:18][CH3:19])=[O:25])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

Participants

Conditions

Temperature: 115 °C

Procedure

A mixture of 5-bromo-1-indanone (5.0 g, 23.7 mmol), DIEA (14.4 mL, 82.9 mmol) and PdCl2(PPh3)2 in n-BuOH (50 mL) was purged with carbon monoxide for 5 min and then stirred under a CO balloon at 115° C. for 2 h. The reaction mixture was allowed to cool to room temperature and filtered through Celite. Solvent evaporation in vacuo followed by filtration on a short column of silica gel and eluted with CH2Cl2 gave the crude product. Chromatography (10% EtOAc in Hexane) afforded butyl 1-oxoindane-5-carboxylate. HPLC/MS: m/z=233.1 (M+1), Rt=3.55 min. 1H NMR (CDCl3): δ 8.18 (1H, s), 8.06 (1H, d, J=8.0 Hz), 7.82 (1H, d, J=8.0 Hz), 4.39 (2H, t, J=6.5 Hz), 3.23 (2H, t, J=6.0 Hz), 2.78 (2H, t, J=6.0 Hz), 1.81 (1H, m), 1.52 (2H, m), 1.02 (3H, t, J=7.0 Hz).

Workup

customwas purged with carbon monoxide for 5 min
temperatureto cool to room temperature
filtrationfiltered through Celite
customSolvent evaporation in vacuo
filtrationfollowed by filtration on a short column of silica gel
washeluted with CH2Cl2
customgave the crude product

Sources & evidence

ORD record: ord-31b9fca402144f25b14927be4cddb57c
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803951B2

Reaction notes

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