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

HRID 1758267

반응식

HRID 1758267 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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.)

출처 및 근거

ORD 기록
ord-bdf67d8b242e491d81cbdd155385c5d8
출처 데이터셋
uspto-grants-1983_02
특허 번호
US04372970

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