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

3-Oxotetrahydrofuran → HCID 89923682, 화합물

HRID 626984
노트
인쇄 미리보기

반응식

HRID 626984 반응식
[Br:1][C:2]1[CH:3]=[N:4][C:5](I)=[N:6][CH:7]=1.C([Li])CCC.[O:14]1[CH2:18][CH2:17][C:16](=[O:19])[CH2:15]1>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:16]2([OH:19])[CH2:17][CH2:18][O:14][CH2:15]2)=[N:6][CH:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 5293923-OxotetrahydrofuranHCID 70066515-Bromo-2-iodopyrimidineHCID 178418339Butyllithium

생성물 1

HCID 89923682HCID 89923682, 화합물수율 25%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
-78 °C

실험 절차

5-Bromo-2-iodopyrimidine (10 g, 35.1 mmol) was dissolved in dry toluene (100 mL) and cooled to −78° C. under N2. n-Butyllithium (2.5M solution in hexanes, 14.7 mL) was added dropwise and the reaction mixture was aged for 30 minutes prior to dropwise addition of oxolan-3-one (2.97 mL, 38.6 mmol). The reaction mixture was stirred at −78° C. for 30 minutes, then allowed to warm to room temperature for 1 h. The reaction mixture was diluted with water (200 mL) and extracted with ethyl acetate (3×200 mL). The combined organic extracts were washed successively with water and brine, then dried over magnesium sulphate. The solvent was removed under reduced pressure to afford a dark yellow oil. The crude material was purified by chromatography on silica (Biotage, 100 g cartridge), eluting with 0-100% ethyl acetate in heptanes, to afford the title compound (2.15 g, 25% at 86% purity) as a yellow oil. δH (500 MHz, DMSO-d6) 9.01 (s, 2H), 5.66 (s, 1H), 3.99-3.93 (m, 2H), 3.88-3.77 (m, 2H), 2.46 (dt, J 12.6, 8.9 Hz, 1H), 2.16 (ddd, J 12.6, 6.4, 3.5 Hz, 1H).

후처리

  1. temperatureto warm to room temperature for 1 h
  2. extractionextracted with ethyl acetate (3×200 mL)
  3. washThe combined organic extracts were washed successively with water and brine
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent was removed under reduced pressure
  6. customto afford a dark yellow oil
  7. customThe crude material was purified by chromatography on silica (Biotage, 100 g cartridge)
  8. washeluting with 0-100% ethyl acetate in heptanes

출처 및 근거

ORD 기록
ord-7d4e0315e0ab45b2837799ef39f27430
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09309243B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트