Water → 1-Methanesulfonyloxy-2-(diethylphosphonomethoxy)ethane

HRID 266235ノート

反応式

HRID 266235 の反応式
[CH2:1]([O:3][P:4]([CH2:9][O:10][CH2:11][CH2:12][OH:13])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].O>C(Cl)Cl>[CH3:21][S:22]([O:13][CH2:12][CH2:11][O:10][CH2:9][P:4]([O:3][CH2:1][CH3:2])([O:6][CH2:7][CH3:8])=[O:5])(=[O:24])=[O:23]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10262588Diethyl 2-hydroxyethoxymethanephosphonate

生成物 1

HCID 145409811-Methanesulfonyloxy-2-(diethylphosphonomethoxy)ethane収率 98%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 2-diethylphosphonomethoxy-1-ethanol (40.7 g, 192 mmol) in 500 mL of CH2Cl2 was cooled to 0° C. and then triethylamine (29.1 g, 288 mmol) was added in one portion, followed by addition of methanesulfonyl chloride (26.4 g, 230 mmol) dropwise over 20 min. The reaction mixture was kept at 0° C. for 0.5 hours and then poured into water. The aqueous phase was extracted with two portions of CH2Cl2 and the combined organic phases dried over MgSO4, filtered and concentrated to afford 54.4 g (98%) of 1-methanesulfonyloxy-2-(diethylphosphonomethoxy)ethane as a clear, pale orange oil. The mesylate could be employed without purification or purified by column chromatography on silica gel (5% methanol in CH2Cl2). 1H NMR (200 MHz, CDCl3): 4.46-4.50 (m,2H), 4.26 (quintet, J=6.8 Hz,4H), 3.92-3.99(m,4H), 3.20 (s,3H), and 1.40 (t, J=7 Hz, 6H).

後処理

  1. extractionThe aqueous phase was extracted with two portions of CH2Cl2
  2. dry with materialthe combined organic phases dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-579ca2d6420448ea9fb89f3d1d01ad38
出典データセット
uspto-grants-1997_07
特許番号
US05650510

反応ノート

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