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

Dimethyl methylphosphonate → Dimethyl 2-oxo-4-(3,4-dimethoxyphenyl)butylphosphonate

HRID 569640
노트
인쇄 미리보기

반응식

HRID 569640 반응식
C([Li])CCC.[CH3:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:23][CH2:24][C:25](OC)=[O:26])[CH:18]=[CH:19][C:20]=1[O:21][CH3:22]>CCCCCC.O1CCCC1.[Cl-].[Na+]>[O:26]=[C:25]([CH2:24][CH2:23][C:17]1[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:15]([O:14][CH3:13])[CH:16]=1)[CH2:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 12958Dimethyl methylphosphonateHCID 520347Methyl 3-(3,4-dimethoxyphenyl)propanoateHCID 178418339Butyllithium

생성물 1

HCID 20147936Dimethyl 2-oxo-4-(3,4-dimethoxyphenyl)butylphosphonate수율 28.5%

시약·촉매·용매 3

HCID 5234Sodium Chloride용매HCID 8028
Tetrahydrofuran
용매
2회
HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

To a mixture cooled at -78° C. of 50 ml of 2.1M n-butyl lithium solution in hexane and 100 ml of tetrahydrofuran, was added dropwise 12.4 g of dimethyl methylphosphonate. The mixture was stirred at -78° C. for 30 minutes, and thereafter 22.4 g of methyl 3-(3,4-dimethoxyphenyl)propionate [synthesized from 3,4-dimethoxycinnamic acid in 2 steps: (a) esterification (HCl--CH3OH) and (b) reduction (Pd/C--H2)] and 100 ml of tetrahydrofuran were added dropwise to the mixture. Then, the reaction was continued at -78° C. for 22 hours. The reaction mixture was poured in 500 ml of saturated aqueous sodium chloride solution. After neutralization and extraction with dichloromethane, the extract was dried and concentrated to give crude product. By purification of the crude product by means of column chromatography (silica gel/hexane:ethyl acetate=1:4), 9.0 g of the above caption compound was obtained.

후처리

  1. waitThen, the reaction was continued at -78° C. for 22 hours
  2. extractionAfter neutralization and extraction with dichloromethane
  3. customthe extract was dried
  4. concentrationconcentrated
  5. customto give crude product
  6. customBy purification of the crude product by means of column chromatography (silica gel/hexane:ethyl acetate=1:4)

출처 및 근거

ORD 기록
ord-8709608733304e8d8035a1795b7ee7de
출처 데이터셋
uspto-grants-1988_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04733002

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트