Ethyl Methanesulfonate → Ethyl (diethoxyphosphoryl)methanesulfonate

HRID 129783

反応式

HRID 129783 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 10934205Ethyl (diethoxyphosphoryl)methanesulfonate収率 70%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-33529eec5d4f4ebf99ed1915cc5ec481
出典データセット
uspto-grants-1995_11
特許番号
US05470845

関連ノート

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