Iodine → 1-Iodo-3-triphenylmethoxy-trans-1-octene

HRID 436121

Reaktionsgleichung

Reaktionsgleichung von HRID 436121
[BH4-].[Na+].CC(=CC)C.B(F)(F)F.[C:12]1([C:18]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:19][CH:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:21]#[CH:22])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[I:40]I>O1CCCC1.COCCOCCOC>[I:40]/[CH:22]=[CH:21]/[CH:20]([O:19][C:18]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Komponenten

8

Edukt 5

HCID 807IodineHCID 6356Boron trifluorideHCID 105532-Methyl-2-buteneHCID 4311764Sodium borohydrideHCID 126753473-Triphenylmethoxy-1-octyne

Produkt 1

HCID 201446361-Iodo-3-triphenylmethoxy-trans-1-octene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8150DiglymeLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a mixture of 0.650 g. (16.91 mole) of sodium borohydride and 3.17 g. (45.2 moles) of 2-methyl-2-butene in 40 ml. of diglyme cooled to -5° C. under an inert atmosphere is added over 15 minutes 3.24 g. (22.6 moles) of boron trifluoride ethereate and the resulting mixture is stirred at 0° C. for 2 hours. To this mixture is then added over 5 minutes 8.32 g. (22.6 moles) of 3-triphenylmethoxy-1-octyne (Example 119) in 10 ml. of diglyme, the cooling bath is removed, and the mixture is stirred at ambient temperatures for 1.5 hours. The mixture is cooled to 0° C. and 6.0 g. of finely divided anhydrous trimethylamine oxide is added over 10 minutes. The cooling bath is removed and the mixture is stirred at ambient temperatures for 0.5 hour. The mixture is then poured into 200 ml. of 15% sodium hydrooxide solution, a solution of 16 g. (63 moles) of iodine in 20 ml. of tetrahydrofuran is added immediately, and the resulting mixture is stirred for 0.5 hour. The organic phase is separated and the aqueous phase is washed with ether. The combined organic phase and washings are decolorized with 5% sodium thiosulfate solution, washed with saturated brine, dried (Na2SO4), and evaporated. The residue is dry-columned chromatographed upon alumina using hexane as eluent and the title compound is isolated as an oil.

Aufarbeitung

  1. additionTo a mixture of 0.650 g
  2. additionis added over 15 minutes 3.24 g
  3. additionTo this mixture is then added over 5 minutes 8.32 g
  4. customof diglyme, the cooling bath is removed
  5. additionof finely divided anhydrous trimethylamine oxide is added over 10 minutes
  6. customThe cooling bath is removed
  7. stirringthe mixture is stirred at ambient temperatures for 0.5 hour
  8. additionThe mixture is then poured into 200 ml
  9. stirringthe resulting mixture is stirred for 0.5 hour
  10. customThe organic phase is separated
  11. washthe aqueous phase is washed with ether
  12. washwashed with saturated brine
  13. dry with materialdried (Na2SO4)
  14. customevaporated
  15. customThe residue is dry-columned chromatographed upon alumina

Quellen und Nachweise

ORD-Eintrag
ord-304f6dd066524317a30345e9e9f6a737
Quelldatensatz
uspto-grants-1977_02
Patentnummer
US04007210

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