Bromide ion → (6Z,9Z,28E,31E)-heptatriaconta-6,9,28,31-tetraen-19-ol

HRID 537832ノート

反応式

HRID 537832 の反応式
[Mg].[Br-].II.[CH:5](=[O:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].Cl>C1COCC1.O>[CH3:23][CH2:22][CH2:21][CH2:20][CH2:19]/[CH:18]=[CH:17]\[CH2:16]/[CH:15]=[CH:14]\[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]([OH:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]/[CH2:15]/[CH:16]=[CH:17]/[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

参加物

8

反応物 5

HCID 259Bromide ionHCID 313Hydrochloric AcidHCID 807IodineHCID 5462224Magnesium2 回HCID 57500215(10Z,13Z)-nonadeca-10,13-dienal

生成物 1

HCID 86684839(6Z,9Z,28E,31E)-heptatriaconta-6,9,28,31-tetraen-19-ol収率 139.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
45 °C

実験手順

A 100 mL round bottom flask, charged with magnesium turnings (355 mg, 14.6 mmol) and a stir bar, was dried with a high temperature heat gun for 5 minutes. Upon cooling under nitrogen, THF (6 mL) was added followed by linolaidyl bromide (6.02 g, 18.3 mmol). The mixture was heated to 45° C. and a single grain of iodine was added. The reaction was refluxed for 2.5 hours then cooled to room temperature where upon a solution of (10Z,13Z)-nonadeca-10,13-dienal (3.4 g, 12.4 mmol) in THF (10 mL) was added. The solution was stirred for 1.5 hours at room temperature then poured into water (150 mL) and 5% HCl (50 mL) was added. Upon dissolution of the magnesium, the solution was extracted with ether (2×150 mL). The combined ether extracts were dried on magnesium sulfate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography (100% hexanes) to afford the title compound as a colorless oil (4.57 g, 71%).

後処理

  1. customwas dried with a high temperature
  2. temperatureheat gun for 5 minutes
  3. temperatureUpon cooling under nitrogen
  4. additionTHF (6 mL) was added
  5. temperatureThe reaction was refluxed for 2.5 hours
  6. additionwas added
  7. additionwas added
  8. extractionthe solution was extracted with ether (2×150 mL)
  9. dry with materialThe combined ether extracts were dried on magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo to dryness
  12. customThe residue was purified by column chromatography (100% hexanes)

出典と根拠

ORDレコード
ord-191b2e4b1fd144799da10cf414f0f371
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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