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

HRID 327009

반응식

HRID 327009 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-861dc23fa4a446a397e572cc47b45efa
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05272128

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