Methanol → HCID 68712505, compound

HRID 29284Notes

Reaction equation

HRID 29284 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[C:9]=2[C:10]=1[CH3:11])=[O:5])C.CO.[Li+].[OH-]>C1COCC1>[C:16]([C:12]1[C:9]2[C:10]([CH3:11])=[C:6]([C:4]([OH:5])=[O:3])[O:7][C:8]=2[CH:15]=[CH:14][CH:13]=1)#[N:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 687167794-Cyano-3-methyl-benzofuran-2-carboxylic acid ethyl ester

Product 1

HCID 68712505HCID 68712505, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 550 mg of 4-cyano-3-methyl-benzofuran-2-carboxylic acid ethyl ester (2.4 mmol) in 15 mL of THF was added 5 mL of MeOH and 5 mL of 1N LiOH. The reaction was complete in 2 h. After quenching with 5 mL of 1 N HCl and work up, 4-cyano-3-methyl-benzofuran-2-carboxylic acid was obtained in quantitative yield. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.7 (s, 3 H) 7.7 (m, 1 H) 7.9 (d, J=7.3 Hz, 1 H) 8.1 (m, 1 H).

Workup

  1. customAfter quenching with 5 mL of 1 N HCl

Sources & evidence

ORD record
ord-09ef1be58cb742e4ae2b62cd2cbb84d3
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

Loading…