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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 512793
ノート
印刷プレビュー

反応式

HRID 512793 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a6a6d7c1575e43f58ad1e0f76445d2f5
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09102648B1

反応ノート

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