Sodium Hydroxide → 5-Cyano-1-benzothiophene-7-carboxylic acid

HRID 749431노트

반응식

HRID 749431 반응식
[C:1]([C:3]1[CH:4]=[C:5]([C:12]([O:14]CC)=[O:13])[C:6]2[S:10][CH:9]=[CH:8][C:7]=2[CH:11]=1)#[N:2].[OH-].[Na+]>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([C:12]([OH:14])=[O:13])[C:6]2[S:10][CH:9]=[CH:8][C:7]=2[CH:11]=1)#[N:2]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 68979189Ethyl 5-cyano-1-benzothiophene-7-carboxylate

생성물 1

HCID 586835225-Cyano-1-benzothiophene-7-carboxylic acid수율 87.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Ethyl 5-cyano-1-benzothiophene-7-carboxylate (5.6 g, 24.3 mmol) was dissolved THF (96 mL) and to the resultant solution was added an aqueous solution of NaOH (1.07 g of NaOH in 14 mL of water, 26.7 mmol) at 0° C. The mixture was stirred at room temperature overnight and then most of the solvent was removed by evaporation. The residue was dissolved in an aqueous solution of NaOH (0.1 M). The solution was washed thrice with chloroform, acidified with 2M HCl and then extracted with ethyl acetate. The organic solution was separated and the solvent was evaporated. The residue was flash chromatographed on silica gel (CH2Cl2-MeOH—NH4OH, 8:2:0.5). There was obtained 4.3 g (85%) of 5-cyano-1-benzothiophene-7-carboxylic acid as a tan solid. 1H NMR (500 MHz, DMSO-d6): 7.7 (d, 1H), 8.1 (d, 2H), 8.3 (d, 1H), 8.7 (s, 1H), 14 (b, 1H); LCMS: m/z 202 (M−1)−.

후처리

  1. custommost of the solvent was removed by evaporation
  2. dissolutionThe residue was dissolved in an aqueous solution of NaOH (0.1 M)
  3. washThe solution was washed thrice with chloroform
  4. extractionextracted with ethyl acetate
  5. customThe organic solution was separated
  6. customthe solvent was evaporated
  7. customchromatographed on silica gel (CH2Cl2-MeOH—NH4OH, 8:2:0.5)

출처 및 근거

ORD 기록
ord-a950e7cc4e5c48dd80367ff413ef359b
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402581B2

반응 노트

불러오는 중…