Triethylamine → Diisopropyl P-[[(2-(difluoromethoxy)-6-methylphenyl)sulfonyloxy]methyl]phosphonate

HRID 327007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 327007
[OH:1][CH2:2][P:3](=[O:12])([O:8][CH:9]([CH3:11])[CH3:10])[O:4][CH:5]([CH3:7])[CH3:6].C(N(CC)CC)C.[CH3:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH:28]([F:30])[F:29])[C:22]=1[S:31](Cl)(=[O:33])=[O:32]>CCOCC.C(OCC)(=O)C.C(Cl)Cl>[F:30][CH:28]([F:29])[O:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([CH3:20])[C:22]=1[S:31]([O:1][CH2:2][P:3](=[O:12])([O:4][CH:5]([CH3:7])[CH3:6])[O:8][CH:9]([CH3:11])[CH3:10])(=[O:33])=[O:32]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 10867235Diisopropyl hydroxymethylphosphonateHCID 189816922-(Difluoromethoxy)-6-methylbenzene-1-sulfonyl chloride

Produkt 1

HCID 18981670Diisopropyl P-[[(2-(difluoromethoxy)-6-methylphenyl)sulfonyloxy]methyl]phosphonate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittel2×HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 20 ml of ether, 8.6 g of diisopropyl P-(hydroxymethyl)phosphonate, prepared in Example 17, and 6.9 ml of triethylamine was added dropwise over 25 minutes to 15.2 g of crude 2-methyl-6-(difluoromethoxy)benzenesulfonyl chloride, prepared in Example 3, in 70 ml of ether. After the mild exotherm, the reaction was allowed to stir overnight at room temperature and was then diluted with 200 ml of ethyl acetate, the resulting ethyl acetate solution washed with two 80 ml portions of water, dried with magnesium sulfate, filtered, and concentrated to yield 10.2 g of the very crude desired product as a black oil. The crude product was dissolved in 10 ml of methylene chloride and flash chromatographed on Merck silica gel using ethyl acetate and hexanes. After combining similar fractions, the desired product was isolated as an amber oil in low yield.

Aufarbeitung

  1. washthe resulting ethyl acetate solution washed with two 80 ml portions of water
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto yield 10.2 g of the very crude desired product as a black oil
  6. customflash chromatographed on Merck silica gel

Quellen und Nachweise

ORD-Eintrag
ord-347013a9bcfd4327a908a0f0c94d540e
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05272128

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