Water → Benzofuran-2-carboxylic acid, 5-cyanomethyl-, ethyl ester

HRID 1758267Notes

Reaction equation

HRID 1758267 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][C:7]=2[CH:16]=1.[C-:17]#[N:18].[Na+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[C:17]([CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][C:7]=2[CH:16]=1)#[N:18]

Participants

6

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 13322225Ethyl 5-(chloromethyl)-1-benzofuran-2-carboxylate

Product 1

HCID 615261Benzofuran-2-carboxylic acid, 5-cyanomethyl-, ethyl esterYield 66.7%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 5-chloromethylbenzofuran-2-carboxylate (3.0 g, 0.0126 mol), sodium cyanide (1.23 g, 0.025 mol), tetrabutylammonium bromide (0.50 g, 0.0013 mol), water (10 cm3) and dichloromethane (10 cm3) was vigorously stirred for 18 hr. at room temperature. The mixture was separated and the organic layer was washed with water, dried (Na2SO4), filtered and the solvent was removed. The residue was recrystallised from petroleum ether (b.p. 60°-80° C.) to give ethyl 5-cyanomethylbenzofuran-2-carboxylate (1.92 g, 0.0084 mol, 66.6%) m.p. 76°-77° C.-t.l.c./silica/toluene, RF 0.11.

Workup

  1. customat room temperature
  2. customThe mixture was separated
  3. washthe organic layer was washed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent was removed
  7. customThe residue was recrystallised from petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-bdf67d8b242e491d81cbdd155385c5d8
Source dataset
uspto-grants-1983_02
Patent number
US04372970

Reaction notes

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