Hydrochloric Acid → 5-Cyano-2-[2-(4-methoxyphenyl)ethyl]-3-benzofurancarboxylic acid

HRID 1901333노트

반응식

HRID 1901333 반응식
[OH-:1].[Na+].BrBr.[C:5]([C:8]1[C:12]2[CH:13]=[C:14]([C:17]#[N:18])[CH:15]=[CH:16][C:11]=2[O:10][C:9]=1[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:7])C.Cl>O.O1CCOCC1>[C:17]([C:14]1[CH:15]=[CH:16][C:11]2[O:10][C:9]([CH2:19][CH2:20][C:21]3[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=3)=[C:8]([C:5]([OH:1])=[O:7])[C:12]=2[CH:13]=1)#[N:18]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24408BromineHCID 218444313-Acetyl-2-[2-(4-methoxyphenyl)ethyl]-5-benzofurancarbonitrile

생성물 1

HCID 218443945-Cyano-2-[2-(4-methoxyphenyl)ethyl]-3-benzofurancarboxylic acid수율 34.6%

시약·촉매·용매 2

HCID 962Water용매2회HCID 312751,4-Dioxane용매

실험 절차

5.2 g of sodium hydroxide was dissolved in 30 ml of water, and the solution was cooled to a temperature of 0° C. or below. With stirring, to this were added dropwise 2.7 ml of bromine and then 40 ml of a dioxane solution containing 4.14 g of 3-acetyl-2-[2-(4-methoxyphenyl)ethyl]-5-benzofurancarbonitrile obtained in the above step d). The resulting mixture was stirred at 0° C. for 45 minutes with ice cooling for 1 hour. The resulting reaction solution was mixed with water, adjusted to pH 2 with concentrated hydrochloric acid, and then extracted with chloroform. The resulting organic layer was washed with water and dried to distill off the solvent. Thereafter, the resulting residue was purified by subjecting it to silica gel column chromatography using chloroform as an eluant, thereby obtaining 1.44 g of 5-cyano-2-[2-(4-methoxyphenyl)ethyl]-3-benzofurancarboxylic acid.

후처리

  1. temperaturethe solution was cooled to a temperature of 0° C. or below
  2. customobtained in the above step d)
  3. stirringThe resulting mixture was stirred at 0° C. for 45 minutes with ice cooling for 1 hour
  4. customThe resulting reaction solution
  5. extractionextracted with chloroform
  6. washThe resulting organic layer was washed with water
  7. customdried
  8. distillationto distill off the solvent
  9. customThereafter, the resulting residue was purified

출처 및 근거

ORD 기록
ord-36f74868d66942b08ce603d343d12f7b
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05576343

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