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

HRID 1440734ノート

反応式

HRID 1440734 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒2 回HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f5ed1d22a68a42038c9a0cb208f3308e
出典データセット
uspto-grants-1996_03
特許番号
US05500405

反応ノート

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