Triethylamine → O-Isopropyl P-Ethyl[[(2,6-dichlorophenyl)sulfonyloxy]methyl]phosphinate

HRID 327009ノート

反応式

HRID 327009 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S:9](Cl)(=[O:11])=[O:10].C(N(CC)CC)C.[CH2:20]([P:22]([CH2:28][OH:29])(=[O:27])[O:23][CH:24]([CH3:26])[CH3:25])[CH3:21]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:20]([P:22]([CH2:28][O:29][S:9]([C:3]1[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])(=[O:11])=[O:10])(=[O:27])[O:23][CH:24]([CH3:26])[CH3:25])[CH3:21]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 5221832,6-DichlorobenzenesulfonylchlorideHCID 15041111O-isopropyl P-ethyl(hydroxymethyl)phosphinate

生成物 1

HCID 54170058O-Isopropyl P-Ethyl[[(2,6-dichlorophenyl)sulfonyloxy]methyl]phosphinate収率 65.4%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 19.6 g of 2,6-dichlorobenzenesulfonyl chloride dissolved in 70 ml of methylene chloride was added dropwise over 40 minutes to a mixture of 25 ml of methylene chloride, 15.0 ml of triethylamine, 1.0 g of DMAP, and 16.5 g of O-isopropyl P-ethyl(hydroxymethyl)phosphinate, (Example 22, Method A). The addition caused a mild exotherm and the reaction was allowed to stir at room temperature overnight. The reaction mixture was then washed with two 50 ml portions of water, the phases separated, the organic phase dried with magnesium sulfate, filtered, and concentrated to yield 19.6 g of the desired product as a yellow oil. The crude product was diluted with 10 ml of methylene chloride and flash chromatographed using blends of ethyl acetate and hexanes. Similar fractions were combined and rechromatographed to yield 0.95 g of the desired product.

後処理

  1. additionThe addition
  2. washThe reaction mixture was then washed with two 50 ml portions of water
  3. customthe phases separated
  4. dry with materialthe organic phase dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-861dc23fa4a446a397e572cc47b45efa
出典データセット
uspto-grants-1993_12
特許番号
US05272128

反応ノート

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