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

HRID 266235노트

반응식

HRID 266235 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 145409811-Methanesulfonyloxy-2-(diethylphosphonomethoxy)ethane수율 98%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-579ca2d6420448ea9fb89f3d1d01ad38
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05650510

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