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

HRID 1440734노트

반응식

HRID 1440734 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 3283Diethyl Ether용매2회HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f5ed1d22a68a42038c9a0cb208f3308e
출처 데이터셋
uspto-grants-1996_03
특허 번호
US05500405

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