Methanol → Ethyl 6-methoxybenzofuran-2-carboxylate

HRID 710331Notes

Reaction equation

HRID 710331 reaction equation
[CH:1]([C:3]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:4]=1[O:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=O.C1CCN2C(=NCCC2)CC1.CO>CCOC(C)=O>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:3]2[CH:1]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[O:5][C:4]=2[CH:12]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 21476959Ethyl 2-(2-formyl-5-methoxyphenoxy)acetate

Product 1

HCID 11830962Ethyl 6-methoxybenzofuran-2-carboxylateYield 93.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of the product of Step A (1.28 g, 5.37 mmol) and DBU (0.3 ml) was heated for 3 h at 160° C. with stirring, cooled to room temperature and dissolved in EtOAc:MeOH mixture (99:1). The mixture was filtered through the silica bead and the filtrate was evaporated to give the title compound (1.11 g; 77%), as colourless solid. 1H-NMR (CDCl3) 1.40 (tr, 3H, J=7.13 Hz); 3.85 (s, 3H); 4.40 (q, 2H, J=7.13, 14.25 Hz); 4.45 (s, 1H); 6.91 (dd, 1H, J=2.25, 8.68 Hz); 7.04 (d, 1H, J=1.87 Hz); 7.51 (d, 1H, J=5.17 Hz),

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe mixture was filtered through the silica bead
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-5a541607e3a34924aa9296a3ce7298a1
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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