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

HRID 1758267

Reaktionsgleichung

Reaktionsgleichung von HRID 1758267
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]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 615261Benzofuran-2-carboxylic acid, 5-cyanomethyl-, ethyl esterAusbeute 66,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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.)

Quellen und Nachweise

ORD-Eintrag
ord-bdf67d8b242e491d81cbdd155385c5d8
Quelldatensatz
uspto-grants-1983_02
Patentnummer
US04372970

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