Dimethylformamide → (10Z,13Z)-nonadeca-10,13-dienal

HRID 537831ノート

反応式

HRID 537831 の反応式
[Mg].[CH2:2](Br)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].CN([CH:24]=[O:25])C>CCOCC>[CH:24](=[O:25])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 5462224MagnesiumHCID 10065142(6Z,9Z)-18-bromooctadeca-6,9-diene

生成物 1

HCID 57500215(10Z,13Z)-nonadeca-10,13-dienal収率 218.2%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

A 100 mL round bottom flask charged with magnesium turnings (462 mg, 19.0 mmol) and a stir bar was dried with a high temperature heat gun for 5 minutes. The flask was cooled to room temperature under nitrogen then charged with THF (25 mL). Linoleyl bromide (1.9 g, 5.76 mmol) was added drop wise and the solution was heated to 45° C. for 3 hours under nitrogen. Upon completion, DMF (1.3 mL, 16.7 mmol) was added slowly and the solution was stirred for 1 hour at room temperature. The solution was diluted with ether (75 mL) and washed with 5% HCl (3×50 mL). The ether solution was dried on magnesium sulfate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography (column: 2″×10″; eluted with 2% ether/hexanes) to afford the title compound as a colorless oil (3.5 g, 83%).

後処理

  1. customwas dried with a high temperature
  2. temperatureheat gun for 5 minutes
  3. additionthen charged with THF (25 mL)
  4. temperaturethe solution was heated to 45° C. for 3 hours under nitrogen
  5. washwashed with 5% HCl (3×50 mL)
  6. dry with materialThe ether solution was dried on magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo to dryness
  9. customThe residue was purified by column chromatography (column
  10. washeluted with 2% ether/hexanes)

出典と根拠

ORDレコード
ord-281f638d2611415e9318ceb4eab96918
出典データセット
uspto-grants-2014_10
特許番号
US08865675B2

反応ノート

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