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Diethyl [Chloro(cyano)methyl]phosphonate → 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl (1R,3S)-3-((Z)-2-chloro-2-cyanovinyl)-2,2-dimethylcyclopropanecarboxylate

HRID 554027
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인쇄 미리보기

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HRID 554027 반응식
CC(C)([O-])C.[K+].[CH3:7][C:8]1([CH3:30])[C@@H:10]([CH:11]=O)[C@H:9]1[C:13]([O:15][CH2:16][C:17]1[C:22]([F:23])=[C:21]([F:24])[C:20]([CH2:25][O:26][CH3:27])=[C:19]([F:28])[C:18]=1[F:29])=[O:14].C(OP([CH:39]([Cl:42])[C:40]#[N:41])(=O)OCC)C>O1CCCC1>[Cl:42]/[C:39](/[C:40]#[N:41])=[CH:11]\[C@@H:10]1[C@@H:9]([C:13]([O:15][CH2:16][C:17]2[C:22]([F:23])=[C:21]([F:24])[C:20]([CH2:25][O:26][CH3:27])=[C:19]([F:28])[C:18]=2[F:29])=[O:14])[C:8]1([CH3:7])[CH3:30]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10750995Diethyl [Chloro(cyano)methyl]phosphonateHCID 23665647Potassium tert-butoxideHCID 866391422,3,5,6-tetrafluoro-4-methoxymethylbenzyl (1R,3S)-2,2-dimethyl-3-formylcyclopropanecarboxylate

생성물 1

HCID 866391412,3,5,6-tetrafluoro-4-methoxymethylbenzyl (1R,3S)-3-((Z)-2-chloro-2-cyanovinyl)-2,2-dimethylcyclopropanecarboxylate수율 32.3%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

A solution of 0.14 g of potassium tert-butoxide in 1 ml of tetrahydrofuran was added dropwise to a mixture of 0.35 g of 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl (1R,3S)-2,2-dimethyl-3-formylcyclopropanecarboxylate, 0.21 g of diethyl(chlorocyanomethyl)phosphonate and 5 ml of anhydrous tetrahydrofuran with ice-cooling under a nitrogen atmosphere. After stirring with ice-cooling for 15 minutes, the reaction mixture was poured into a saturated saline solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.13 g of 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl (1R,3S)-3-((Z)-2-chloro-2-cyanovinyl)-2,2-dimethylcyclopropanecarboxylate represented by the formula (1):

후처리

  1. temperaturecooling under a nitrogen atmosphere
  2. temperaturecooling for 15 minutes
  3. additionthe reaction mixture was poured into a saturated saline solution
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-81c8faf881574b0d91a1725f2768df66
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08048916B2

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