Iodine → 5,5-Dimethyl-1-iodo-trans-octen-3-ol

Reaktionsgleichung

[CH3:1][C:2]([CH3:17])([CH2:14][CH2:15][CH3:16])[CH2:3][CH:4]([O:7]C1CCCCO1)[C:5]#[CH:6].C(BC(C(C)C)C)(C(C)C)C.C[N+]([O-])(C)C.[OH-].[Na+].[I:36]I.O1CCCC1CC(O)=O.O>COCCOCCOC>[CH3:1][C:2]([CH3:17])([CH2:14][CH2:15][CH3:16])[CH2:3][CH:4]([OH:7])/[CH:5]=[CH:6]/[I:36]

Komponenten

Edukt 6

HCID 807Iodine

HCID 1145Trimethylamine oxide

HCID 14798Sodium Hydroxide

HCID 192733Bis(1,2-dimethylpropyl)borane

HCID 538897305,5-Dimethyl-3-tetrahydropyranyloxy-1-octyne

HCID 86732972Tetrahydrofuranacetic acid water

Produkt 1

Versuchsvorschrift

Treatment of 23.8 g. (0.100 mole) of 5,5-dimethyl-3-tetrahydropyranyloxy-1-octyne (Example 999) successively with 233 ml. of 0.43 M disiamylborane in diglyme, 22.5 g. of trimethylamine oxide, 150 ml. of 1 N sodium hydroxide, 25.4 g. of iodine, and 900 ml. of 3:1:1 tetrahydrofuranacetic acid-water as described in Example 996 gives the title compound.