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Pyridine → HCID 91170071、化合物

HRID 132735
ノート
印刷プレビュー

反応式

HRID 132735 の反応式
[CH2:1]([C:6]([CH:11]([CH3:13])[CH3:12])([CH2:9][OH:10])[CH2:7][OH:8])[CH2:2][CH:3]([CH3:5])[CH3:4].[O:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.N1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:25](Cl)(=[O:34])[CH:26]=[CH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O>[C:18]([O:8][CH2:7][C:6]([CH2:1][CH2:2][CH:3]([CH3:5])[CH3:4])([CH:11]([CH3:13])[CH3:12])[CH2:9][O:10][C:25](=[O:34])[CH:26]=[CH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:14])[CH:17]=[CH:16][C:15]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 660233-Phenylprop-2-enoyl chlorideHCID 117453912-(3-Methylbutyl)-2-(propan-2-yl)propane-1,3-diol

生成物 1

HCID 91170071HCID 91170071、化合物収率 51%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To 7.5 g (0.04 mol) 2-isoamyl-2-isopropyl-1,3-propandiol, which was prepared according to the process described in synthetic example 63, was added 50 ml tetrahydrofuran, then added 9.7 ml (0.12 mol) pyridine with stirring. To the resulting homogenous mixture was slowly added 16.7 g(0.1 mol) cinnamoyl chloride. The mixture was stirred at room temperature for 1 hour, and heated refluxing for 4 hours. Upon completing the reaction, 50 ml water was added to dissolve the resulting salt. The mixture was extracted with ethyl acetate. The organic phase was separated, washed with saturated saline for two times, and dried over anhydrous sodium sulfate. The solvent was removed. Column chromatography gave 2-isoamyl-2-isopropyl-1,3-propandiol dicinnamate as a yellow viacous liquid, and the yield was 51%. 1HNMR: δ (ppm) 0.88(d, 6H, CH3 of isoamyl), 0.99(d, 6H, CH3 of isopropyl), 1.21(m, 2H, CH2 of isoamy), 1.47(m, 2H, CH2 of isoamyl), 1.51(m, 1H, CH of isoamyl), 1.96(m, 1H, CH of isopropyl), 4.26(m, 4H, CH2O of 1,3-propandiol), 6.45(d, 2H, CH linked to carbonyl), 7.26-7.70(m, 12H, ArH and ═CH—)

後処理

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. temperatureheated
  3. temperaturerefluxing for 4 hours
  4. additionwas added
  5. dissolutionto dissolve the resulting salt
  6. extractionThe mixture was extracted with ethyl acetate
  7. customThe organic phase was separated
  8. washwashed with saturated saline for two times
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was removed

出典と根拠

ORDレコード
ord-26e817e428844f62875793870be909ba
出典データセット
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07388061B2

反応ノート

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