Ethyl Acetate → HCID 57949601, compound

HRID 2427746Notes

Reaction equation

HRID 2427746 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1)[CH2:7]2.C[O-].[Na+].CO.[C:30](OCC)(=[O:32])C>CO.CCCCCC>[CH3:1][C:2]1[CH:3]=[C:4]([O:32][CH3:30])[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1)[CH2:7]2

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 11560384HCID 11560384, compoundHCID 23694274Sodium methanolate methanol

Product 1

HCID 57949601HCID 57949601, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7-methyl-5-bromo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.100 g, 0.25 mmol), 30% sodium methoxide-methanol (0.5 mL), and CuBr (0.005 g, 0.04 mmol) in methanol (4 mL) was stirred at 100° C. for 1 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 7-methyl-5-methoxy-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.035 g, 41%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.80 (s, 3H), 3.91 (s, 3H), 4.26 (s, 2H), 4.83 (s, 2H), 6.82 (d, 2H), 7.26 (d, 2H), 7.42 (d, 2H).

Sources & evidence

ORD record
ord-bdf596ef011c4b0cbb75d202b568c0cd
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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