Toluene → HCID 59859868、化合物

HRID 1944555ノート

反応式

HRID 1944555 の反応式
C(O[C:4](=[O:17])[C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:9][CH:8]=1)C.[NH2:18][C:19]1[CH:20]=[N:21][C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2.C[Al](C)C.C1(C)C=CC=CC=1>ClCCCl.C(OCC)C.CO>[N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[C:19]([NH:18][C:4](=[O:17])[C:5]#[C:6][C:7]2[CH:8]=[CH:9][C:10]([C:13]([CH3:14])([CH3:15])[CH3:16])=[CH:11][CH:12]=2)[CH:20]=1

参加物

8

反応物 4

HCID 1140TolueneHCID 113753-AminoquinolineHCID 11333698Ethyl 3-(4-tert-Butylphenyl)propiolateHCID 16682925Trimethylaluminum

生成物 1

HCID 59859868HCID 59859868、化合物

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 887Methanol溶媒HCID 3283Diethyl Ether溶媒

実験手順

A solution of (4-tert-butyl-phenyl)-propynoic acid ethyl ester (0.23 g, 1.0 mmol) and 3-aminoquinoline (0.144 g, 1.0 mmol) in 1,2-dichloroethane (15 mL) was treated with a 2N solution of trimethylaluminum in toluene (0.75 mL, 1.5 mmol). The resultant solution was stirred at room temperature for 15 minutes, then heated at reflux for 18 h. The solution was cooled and treated with methanol (0.50 mL). The product was preabsorbed onto silica gel and purified by flash chromatography, using a gradient of methanol in dichloromethane as the eluant. The product was isolated, after trituration in diethyl ether, as a colorless solid, 0.17 g (52%). MS: m/z 329.2 (MH+). 1HNMR (DMSO-d6): δ 1.31 (s, 9 H), 7.54-7.72 (m, 6 H), 7.97 (d, 1 H), 8.72 (d, 1 H), 8.96 (d, 1 H) and 11.3 (s, 1 H).

後処理

  1. temperatureheated
  2. temperatureat reflux for 18 h
  3. temperatureThe solution was cooled
  4. customThe product was preabsorbed onto silica gel
  5. custompurified by flash chromatography
  6. customThe product was isolated

出典と根拠

ORDレコード
ord-9e4bdf28025f4464bccd7795c172fc72
出典データセット
uspto-grants-2013_03
特許番号
US08394828B2

反応ノート

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