홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Toluene → 4-(2,4-difluorophenyl)pent-4-enoic Acid

HRID 512801
노트
인쇄 미리보기

반응식

HRID 512801 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)[CH2:10][CH2:11][C:12]([OH:14])=[O:13].[C:16]1(C)C=CC=CC=1.[I-].CP(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[Na+]>O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[CH2:16])[CH2:10][CH2:11][C:12]([OH:14])=[O:13]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 1140TolueneHCID 27740813-(2,4-Difluorobenzoyl)propionic AcidHCID 23676156Sodium t-butoxideHCID 178503021HCID 178503021, 화합물

생성물 1

HCID 111173524-(2,4-difluorophenyl)pent-4-enoic Acid

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
52.5 °C

실험 절차

To a mixture of 4-(2,4-difluorophenyl)-4-oxobutanoic acid (100 g) and toluene (1000 ml), added methyl triphenylphosphine iodide (377.5 g) and sodium tertiary butoxide (183 g) at 25-30° C. Heated the reaction mixture to 50-55° C. and stirred for 6-8 hours at the same temperature. After completion of the reaction, cooled the reaction mixture to 25-30° C. Water was added to the reaction mixture and both organic and aqueous layers were separated. pH of aqueous layer was adjusted to 11 using 50% hydrochloric acid. Extracted the aqueous layer with toluene and washed the aqueous layer with dichloromethane. pH of the aqueous layer was further adjusted to 2.5 using 50% HCl and the reaction mixture was stirred for 45 minutes. Filtered the obtained solid, washed with water and then dried to get the title compound. Cyclohexane (500 ml) was added to the obtained solid and heated to 45-50° C. Carbon (10 g) was added to the reaction mixture and stirred for 15 minutes. Filtered the reaction mixture and washed with hot cyclohexane. Distilled off half of the solvent under reduced pressure. Cooled the reaction mixture to 10-15° C. and stirred for 60 minutes at the same temperature. Filtered the solid and washed with chilled cyclohexane and dried to get the title compound. Yield: 65.75 g

후처리

  1. customAfter completion of the reaction
  2. temperaturecooled the reaction mixture to 25-30° C
  3. customboth organic and aqueous layers were separated
  4. extractionExtracted the aqueous layer with toluene
  5. washwashed the aqueous layer with dichloromethane
  6. stirringthe reaction mixture was stirred for 45 minutes
  7. filtrationFiltered the obtained solid
  8. washwashed with water
  9. customdried

출처 및 근거

ORD 기록
ord-52d0ffe9d15b42e2a5f6fc83d6e83be8
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09102664B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트