Iodine → HCID 19885920, Verbindung

HRID 654916

Reaktionsgleichung

Reaktionsgleichung von HRID 654916
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].BrCCCCCCCCCCCCCCCCCC.[Mg].II.[CH3:43][Si:44]([CH3:53])([CH3:52])[C:45]1[O:49][CH:48]=[C:47]([CH:50]=[O:51])[CH:46]=1>C(OCC)C.O1CCCC1>[OH:51][CH:50]([C:47]1[CH:46]=[C:45]([Si:44]([CH3:53])([CH3:52])[CH3:43])[O:49][CH:48]=1)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

Komponenten

8

Edukt 5

HCID 807IodineHCID 82181-BromooctadecaneHCID 5462224MagnesiumHCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 178442890HCID 178442890, Verbindung

Produkt 1

HCID 19885920HCID 19885920, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of octadecylmagnesium bromide (10.2 ml of a 0.34M solution in ethyl ether, 3.46 mmol, generated from 1-bromooctadecane and magnesium using iodine as an initiator) at 0° under argon, was added dropwise 5-trimethylsilyl-3-furaldehyde (0.265 g., 1.57 mmol) in 2 ml tetrahydrofuran. This solution was allowed to warm to room temperature, stirred for 30 minutes, and quenched with a 5% ammonium chloride solution. The resulting mixture was partitioned between ethyl ether and 5% sodium bicarbonate. The organic portion was washed with 10% sodium bisulfite, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give a residue. This was taken up in ethyl ether and filtered. The ether portion was concentrated to give a waxy residue which was purified by flash chromatography (silica, 10% ethyl ether/petroleum ether) to give the desired alcohol.

Aufarbeitung

  1. customat 0°
  2. customquenched with a 5% ammonium chloride solution
  3. customThe resulting mixture was partitioned between ethyl ether and 5% sodium bicarbonate
  4. washThe organic portion was washed with 10% sodium bisulfite, water, saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a residue
  9. filtrationfiltered
  10. concentrationThe ether portion was concentrated
  11. customto give a waxy residue which
  12. customwas purified by flash chromatography (silica, 10% ethyl ether/petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-d47716d1b7bf40a5b7827c0ea24393c5
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05134128

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