Ethyl Methanesulfonate → Ethyl (diethoxyphosphoryl)methanesulfonate

HRID 129783

반응식

HRID 129783 반응식
[CH3:1][S:2]([O:5][CH2:6][CH3:7])(=[O:4])=[O:3].[Li]CCCC.[P:13](Cl)([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])=[O:14].[Cl-].[NH4+]>C1COCC1.CCCCCC>[CH2:16]([O:15][P:13]([CH2:1][S:2]([O:5][CH2:6][CH3:7])(=[O:4])=[O:3])([O:18][CH2:19][CH3:20])=[O:14])[CH3:17]

참가 물질

7

반응물 4

HCID 6113Ethyl MethanesulfonateHCID 13139Diethyl chlorophosphateHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

생성물 1

HCID 10934205Ethyl (diethoxyphosphoryl)methanesulfonate수율 70%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

A solution of ethyl methanesulfonate (4.27 mL, 40.3 mmol) in 100 mL of dry THF was treated at -78° C. with 19.3 mL (44.4 mmol) of n-BuLi in hexane. After 15 min. diethyl chlorophosphate (3.30 ml, 22.2 mmol) was added. The solution was kept at -78° C. for 0.5 h and allowed to stay at -50° C. for 1 h. Saturated ammonium chloride (75 mL) was added to the solution and the mixture warmed to room temperature. The mixture was concentrated (THF removed), diluted with water and extracted with methylene chloride (3×70 mL). The combined organic fractions were dried (MgSO4), concentrated and purified by distillation to yield 3.86 g (70%) of title compound.

후처리

  1. waitto stay at -50° C. for 1 h
  2. concentrationThe mixture was concentrated
  3. custom(THF removed)
  4. additiondiluted with water
  5. extractionextracted with methylene chloride (3×70 mL)
  6. dry with materialThe combined organic fractions were dried (MgSO4)
  7. concentrationconcentrated
  8. distillationpurified by distillation

출처 및 근거

ORD 기록
ord-33529eec5d4f4ebf99ed1915cc5ec481
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05470845

연결된 노트

불러오는 중…