Ethyl Methanesulfonate → Ethyl (diethoxyphosphoryl)methanesulfonate

HRID 552706

反応式

HRID 552706 の反応式
[CH3:1][S:2]([O:5][CH2:6][CH3:7])(=[O:4])=[O:3].C1COCC1.C([Li])CCC.[P:18](Cl)(=[O:25])([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21]>CCCCCC>[CH2:6]([O:5][S:2]([CH2:1][P:18]([O:22][CH2:23][CH3:24])([O:19][CH2:20][CH3:21])=[O:25])(=[O:4])=[O:3])[CH3:7]

参加物

6

反応物 4

HCID 6113Ethyl MethanesulfonateHCID 8028TetrahydrofuranHCID 13139Diethyl chlorophosphateHCID 178418339Butyllithium

生成物 1

HCID 10934205Ethyl (diethoxyphosphoryl)methanesulfonate

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

To a solution of methanesulfonic acid, ethyl ester (11.00 mL, 0.1068 mol) in THF (200.0 mL, 2.466 mol) at −78° C. was added 2.500 M of n-butyllithium in hexane (50.00 mL) over 15 minutes and the mixture was stirred for 20 minutes. Phosphorochloridic acid, diethyl ester (10.0 mL, 0.0694 mol) was added to the mixture at −78° C. The mixture was stirred for 3.5 hours, allowing to warm to 0° C. The reaction was quenched with 5M ammonium chloride in water (100 mL) and the mixture was concentrated in vacuo to remove THF. The aqueous was extracted with EtOAc (2×150 mL) and the organics were combined and concentrated in vacuo. The product was purified by flash chromatography (0 to 100% EtOAc/Hexanes) to yield the product as an oil (9.07 g, 50%+10.4 g of a mixed fraction).

後処理

  1. stirringThe mixture was stirred for 3.5 hours
  2. customThe reaction was quenched with 5M ammonium chloride in water (100 mL)
  3. concentrationthe mixture was concentrated in vacuo
  4. customto remove THF
  5. extractionThe aqueous was extracted with EtOAc (2×150 mL)
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by flash chromatography (0 to 100% EtOAc/Hexanes)

出典と根拠

ORDレコード
ord-c3cf5c1b93fe4367a459d70d4197a2f1
出典データセット
uspto-grants-2011_05
特許番号
US07951810B2

関連ノート

読み込み中…