Dodecanal → 4-(5-Hydroxy-3-hexadecynyl)-2-triethylsilylfuran

HRID 488224Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 488224
C([Li])CCC.Br[C:7](Br)=[CH:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([Si:16]([CH2:21][CH3:22])([CH2:19][CH3:20])[CH2:17][CH3:18])[O:14][CH:15]=1.[CH:24](=[O:36])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>O1CCCC1>[OH:36][CH:24]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:7]#[C:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([Si:16]([CH2:21][CH3:22])([CH2:19][CH3:20])[CH2:17][CH3:18])[O:14][CH:15]=1

Komponenten

5

Edukt 3

HCID 8194DodecanalHCID 150371054-(4,4-Dibromo-3-butenyl)-2-triethylsilylfuranHCID 178418339Butyllithium

Produkt 1

HCID 150371064-(5-Hydroxy-3-hexadecynyl)-2-triethylsilylfuran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

n-Butyl lithium (a 2.5M solution in tetrahydrofuran; 0.42 ml, 1.04 mmol) was added dropwise to a solution of 4-(4,4-dibromo-3-butenyl)-2-triethylsilylfuran (200 mg, 0.51 mmol) in tetrahydrofuran (8 ml) at -78 degrees under argon. After 2 hours, a solution of 1-dodecanal (102 mg, 0.56 mmol) in tetrahydrofuran (1 ml) was added. Stirring was continued for 14 hours, while the cooling bath attained room temperature. The mixture was quenched with water and was extracted with ethyl ether. Evaporation of the dried (magnesium sulfate) extracts gave a residue, which was purified by a silica column with 15% ethyl ether/hexane to give the titled alcohol.

Aufarbeitung

  1. waitwas continued for 14 hours, while the cooling bath attained room temperature
  2. customThe mixture was quenched with water
  3. extractionwas extracted with ethyl ether
  4. customEvaporation of the
  5. dry with materialdried (magnesium sulfate)
  6. customextracts gave a residue, which
  7. customwas purified by a silica column with 15% ethyl ether/hexane

Quellen und Nachweise

ORD-Eintrag
ord-ffd20763177845c492680f7c583d8759
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05298633

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