Hydrochloric Acid → (6Z,16Z)-12-((Z)-dec-4-enyl)docosa-6,16-dien-11-ol

HRID 530157

Reaktionsgleichung

Reaktionsgleichung von HRID 530157
[Mg].Br[CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH2:13]([CH:23]([CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]\[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:24]=[O:25])[CH2:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].Cl>O1CCCC1>[CH2:13]([CH:23]([CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]\[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:24]([OH:25])[CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 5462224MagnesiumHCID 10932932(Z)-1-Bromo-4-deceneHCID 89768339HCID 89768339, Verbindung

Produkt 1

HCID 89775018(6Z,16Z)-12-((Z)-dec-4-enyl)docosa-6,16-dien-11-olAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a suspension of magnesium turnings (0.6 g, 23.9 mmol) in tetrahydrofuran (5 mL) was slowly added a solution of (Z)-1-bromodec-4-ene 3 (4.5 g, 20.5 mmol) in tetrahydrofuran (5 mL). The reaction mixture was stirred for 30 minutes at room temperature then a solution of (Z)-2-((Z)-dec-4-enyl)dodec-6-enal 7 in tetrahydrofuran (5 mL) was added. The solution was stirred for 15 minutes at room temperature then poured into 5% hydrochloric acid (50 mL) and ice (100 mL). The solution was extracted with ether (2×150 mL). The combine ether extracts were dried on magnesium sulfate, filtered, and concentrated in vacuo to dryness. The residue was purified by column chromatography (1% ethyl acetate in hexanes) to afford (6Z,16Z)-12-((Z)-dec-4-enyl)docosa-6,16-dien-11-ol 8 as a colorless oil (4.8 g, 76%). Rf 0.45 (10% EtOAc-Hexanes).

Aufarbeitung

  1. stirringThe solution was stirred for 15 minutes at room temperature
  2. extractionThe solution was extracted with ether (2×150 mL)
  3. dry with materialThe combine ether extracts were dried on magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to dryness
  6. customThe residue was purified by column chromatography (1% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-5fb82f821f6f41ffa5b365403468eadd
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09352042B2

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