Trifluoroacetic acid → HCID 46914013, compound

HRID 597846Notes

Reaction equation

FC(F)(F)[C:3](O)=[O:4].[CH2:8]([O:10][C:11](=[O:24])[CH2:12][CH2:13][C:14]1[C:22]2[C:21](=[O:23])[CH2:20][CH2:19][CH2:18][C:17]=2[NH:16][CH:15]=1)[CH3:9].COC(OC)OC.[OH-].[Na+]>O.C(OCC)(=O)C>[CH2:8]([O:10][C:11](=[O:24])[CH2:12][CH2:13][C:14]1[C:22]2[C:21](=[O:23])[CH2:20][CH2:19][CH2:18][C:17]=2[NH:16][C:15]=1[CH:3]=[O:4])[CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

To a trifluoroacetic acid solution (47 mL) containing 3-(3-ethoxy-3-oxopropyl)-4-oxo-4,5,6,7-tetrahydro-1H-indole (4, 10.0 g, 42.5 mmol) was added with trimethylorthoformate (13.6 g, 128 mmol) at 0° C. The reaction was stirred at 0° C. for 30 min, warmed up to room temperature and stirred for 2.0 h. The solution was added with ethyl acetate (250 mL), water (200 mL) and NaOH (18 g). The organic layer was collected and washed with saturated aqueous NaHCO3 (200 mL), dried over MgSO4 (s), and concentrated under reduced pressure. The oily residue was purified by gravity column chromatography (50% EtOAc in hexanes) to give 3-(3-ethoxy-3-oxopropyl)-2-formyl-4-oxo-4,5,6,7-tetrahydro-1H-indole (5, 2.1 g, 8.0 mmol) as yellow solids in 19% yield.

Workup

temperaturewarmed up to room temperature
stirringstirred for 2.0 h
customThe organic layer was collected
washwashed with saturated aqueous NaHCO3 (200 mL)
dry with materialdried over MgSO4 (s)
concentrationconcentrated under reduced pressure
customThe oily residue was purified by gravity column chromatography (50% EtOAc in hexanes)

Sources & evidence

ORD record: ord-9e917815dc6a42dea3435fc387666331
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897602B2

Reaction notes

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