Water → HCID 54322293、化合物

HRID 974737ノート

反応式

HRID 974737 の反応式
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[CH:9][CH:10]=[CH:11][CH2:12][CH2:13][CH2:14][CH3:15].[OH2:16]>CO>[CH2:15]([OH:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=[CH:7][CH:6]=[CH:5][CH2:4][CH2:3][CH2:2][CH3:1]

参加物

4

反応物 2

HCID 962WaterHCID 72729313HCID 72729313、化合物

生成物 1

HCID 54322293HCID 54322293、化合物収率 66%

試薬・触媒・溶媒 1

HCID 887Methanol触媒

実験手順

The pentadecadiene (D) (5.9 g) in 200 ml methanol containing eight drops concentrated HCl was refluxed for 15 minutes. After the solution was cooled, 400 ml of water were added, and the mixture was extracted three times with hexane. The hexane extract was dried over sodium sulfate, and the hexane was removed with a rotary evaporator leaving 3.1 g of crude 8,10-pentadecadienol, which was purified by silica gel liquid chromatography. Unwanted side products were eluted with 10% ether/hexane, and the alcohol was eluted with 50% ether/hexane, giving 2.5 g (66% yield based on the decenenitrile (B)). 8,10-Pentadecadienol in 75 ml pyridine and 5 ml acetic anhydride was refluxed 1.5 hours. After the solution was cooled, 200 ml hexane was added, and the mixture was extracted successively with water, 6N hydrochloric acid (twice), and water. The pentane phase was dried over sodium sulfate, filtered, and the pentane was removed by rotary evaporation, leaving crude product, which was purified by silica gel liquid chromatography (elution in 10% ether/hexane); the yield was 2.8 g (94% based on the alcohol). The product was 39% EE and 61% EZ by GC analysis.

後処理

  1. temperatureAfter the solution was cooled
  2. extractionthe mixture was extracted three times with hexane
  3. extractionThe hexane extract
  4. dry with materialwas dried over sodium sulfate
  5. customthe hexane was removed with a rotary evaporator

出典と根拠

ORDレコード
ord-56b61b424f0640c3a83e4d40424ad8b5
出典データセット
uspto-grants-1997_03
特許番号
US05607670

反応ノート

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