Hydrochloric Acid → Ethyl 5-fluoro-2-(4-fluorophenyl)-2,3-dihydro-1-oxo-1H-indene-2-acetate

HRID 1768938Notes

Reaction equation

[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH:8]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[CH2:7]2.Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].Cl>CN(C=O)C>[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[C:8]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:7]2

Participants

Conditions

Temperature: 10 °C

Procedure

To a solution of 0.720 g (0.018 mol) of 60% sodium hydride suspended in 50 mL DMF at 10° C. was added dropwise 4.0 g (0.0164 mol) of the product from step B dissolved in 25 mL DMF. The reaction mixture was stirred at 10° C. for 20 min. and 3.1 g (0.0164 mol) ethyl bromoacetate was added all at once. The reaction was heated at 60° C. for 15 min, cooled to room temperature, poured into 200 mL 10% HCl, extracted with ethyl acetate (3×50 mL), washed with brine (1×100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to afford 4.0 g of a viscous oil. 1H NMR (CDCl3) δ: 1.10 (t, 3H), 3.18 (s, 2H), 3.63 (s, 2H), 4.18 (q, 2H), 6.95-7.30 (m, 6H), 7.80 (dd, 1H). IR (neat): 1720, 1676 cm-1 .

Workup

temperatureThe reaction was heated at 60° C. for 15 min
temperaturecooled to room temperature
extractionextracted with ethyl acetate (3×50 mL)
washwashed with brine (1×100 mL)
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-6c905d672eea4e0984a9dce07f3a9a53
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05380718

Reaction notes

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