Pyridine → 2,4-Pentanediol monobenzoate monocinnamate

HRID 132710

反応式

HRID 132710 の反応式
[CH3:1][CH:2]([OH:7])[CH2:3][CH:4]([OH:6])[CH3:5].N1C=CC=CC=1.[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH2:23](Cl)[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[O:33]1CCCC1>>[C:23]([O:6][CH:4]([CH3:5])[CH2:3][CH:2]([O:7][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:1])(=[O:33])[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

参加物

6

反応物 5

HCID 1049Pyridine2 回HCID 7412Benzoyl chlorideHCID 8028Tetrahydrofuran2 回HCID 122622,4-PentanediolHCID 94242Benzene, (3-chloro-1-propenyl)-

生成物 1

HCID 858565292,4-Pentanediol monobenzoate monocinnamate収率 89%

実験手順

To 0.03 mol 2,4-pentanediol were added 30 ml tetrahydrofuran and 0.04 mol pyridine, then added 0.03 mol benzoyl chloride with stirring. The reaction was heated refluxing for 4 hours, cooled. Then to the reaction were added 20 ml tetrahydrofuran and 0.05 mol pyridine, followed by 0.04 mol cinnamyl chloride with stirring. The reaction was heated refluxing for 4 hours, cooled and added 20 ml saturated saline. The reaction mixture was extracted with ethyl acetate, and the extract was dried over anhydrous sodium sulfate, filtered. After removing solvent, the crude was purified by column chromatography to give 2,4-pentanediol monobenzoate monocinnamate as a colorless liquid. The yield was 89%. 1HNMR: δ (ppm) 0.8-1.4(8H, m, CH3), 1.9-2.1(1H, m, CH), 5.1-5.3(2H, m, CH linked to ester radical), 6.2-8.0(12H, m, ArH and ═CH—)

後処理

  1. temperatureThe reaction was heated
  2. temperaturerefluxing for 4 hours
  3. temperaturecooled
  4. stirringwith stirring
  5. temperatureThe reaction was heated
  6. temperaturerefluxing for 4 hours
  7. temperaturecooled
  8. additionadded 20 ml saturated saline
  9. extractionThe reaction mixture was extracted with ethyl acetate
  10. dry with materialthe extract was dried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. customAfter removing solvent
  13. customthe crude was purified by column chromatography

出典と根拠

ORDレコード
ord-cb7a91e2125e4369bbec1f28d17a9e49
出典データセット
uspto-grants-2008_06
特許番号
US07388061B2

関連ノート

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