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

HRID 1758267

反応式

HRID 1758267 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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.)

出典と根拠

ORDレコード
ord-bdf67d8b242e491d81cbdd155385c5d8
出典データセット
uspto-grants-1983_02
特許番号
US04372970

関連ノート

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