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Diethyl Ether → 3,5-dimethyl-benzoic acid N'-[1-(2-ethyl-3-methoxy-phenyl)-vinyl]-N-(2-hydroxy-1,1-dimethyl-ethyl)-hydrazide

HRID 39656
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HRID 39656 반응식
C([Si](C)(C)[O:6][CH2:7][C:8]([N:11]([C:25](=[O:34])[C:26]1[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH3:33])[CH:27]=1)[NH:12][C:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[C:15]=1[CH2:22][CH3:23])([CH3:10])[CH3:9])(C)(C)C.[F-].[CH2:38]([N+](CCCC)(CCCC)CCCC)CCC.CCOCC>C1COCC1>[CH2:22]([C:15]1[C:16]([O:20][CH3:21])=[CH:17][CH:18]=[CH:19][C:14]=1[C:13]([NH:12][N:11]([C:8]([CH3:9])([CH3:10])[CH2:7][OH:6])[C:25](=[O:34])[C:26]1[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH3:33])[CH:27]=1)=[CH2:38])[CH3:23]
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참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 2724141Tetrabutylammonium FluorideHCID 103917072-ethyl-3-methoxy-benzoic acid N'-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-N'-(3,5'-dimethyl-benzoyl)-hydrazide

생성물 1

HCID 667643543,5-dimethyl-benzoic acid N'-[1-(2-ethyl-3-methoxy-phenyl)-vinyl]-N-(2-hydroxy-1,1-dimethyl-ethyl)-hydrazide수율 67%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

2.78 g (0.00526 mol) of 2-ethyl-3-methoxy-benzoic acid N′-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-N′-(3,5-dimethyl-benzoyl)-hydrazide were dissolved in 24 mL of THF. The mixture was cooled in an ice bath and 6.0 mL (0.006 mol) of a 1 M tetrabutyl ammonium fluoride solution in THF were added. The reaction was stirred at room temperature for 5-6 hours, and then 100 mL of Et2O were added and the reaction mixture was poured into ice water in a separatory funnel. The aqueous layer was further extracted twice with 25 mL of Et2O and the total ether layer was dried and concentrated. TLC of the product showed a new product (Rf 0.20) below some of the starting material. The product was purified by chromatography, eluting with 40-50% ethyl acetate/hexane to yield 1.42 g of pure 3,5-dimethyl-benzoic acid N′-[1-(2-ethyl-3-methoxy-phenyl)-vinyl]-N-(2-hydroxy-1,1-dimethyl-ethyl)-hydrazide. (67% yield). TLC: Rf=0.20. 1H NMR (CDCl3, 300 MHz) δ (ppm): 7.1-6.8 (m, 5H), 6.0 (d, 1H), 4.3 (d, 1H), 3.78 (s, 3H), 3.5 (d 1H), 2.4 (d, 1H) 2.29 (s, 6H), 2.2 (d, H), 1.56 (s, 3H), 1.45 (s, 3H), 1.00 (t, 3H).

후처리

  1. temperatureThe mixture was cooled in an ice bath
  2. extractionThe aqueous layer was further extracted twice with 25 mL of Et2O
  3. dry with materialthe total ether layer was dried
  4. concentrationconcentrated
  5. customThe product was purified by chromatography
  6. washeluting with 40-50% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-0c9a7968012945cdbaeba32dc78d89a4
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08524948B2

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