Ethyl Acetate → HCID 57949304, compound

HRID 2427745Notes

Reaction equation

HRID 2427745 reaction equation
[CH2:1]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=2)[C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].CO.[C:24](OCC)(=[O:26])C>CO.CCCCCC>[CH2:1]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:26][CH3:24])[CH:14]=2)[C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 231582302-Benzyl-5-bromo-2,3-dihydro-1H-isoindol-1-oneHCID 23694274Sodium methanolate methanol

Product 1

HCID 57949304HCID 57949304, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-benzyl-5-bromo-2,3-dihydro-isoindol-1-one (0.065 g, 0.22 mmol), 30% sodium methoxide-methanol (0.06 mL, 0.33 mmol), and CuBr (0:004 g, 0.03 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 2-benzyl-5-methoxy-2,3-dihydro-isoindol-1-one (0.03 g, 54%). 1H NMR (300 MHz, CDCl3): δ (ppm) 3.86 (s, 3H), 4.22 (s, 2H), 4.78 (s, 2H), 6.82-7.29 (m, 7H), 7.79 (d, 1H).

Sources & evidence

ORD record
ord-ebaf21c74005425d8dd9caa6b40383b1
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

Loading…