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

HRID 436111

Reaktionsgleichung

Reaktionsgleichung von HRID 436111
[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

8

Edukt 6

HCID 807IodineHCID 1145Trimethylamine oxideHCID 14798Sodium HydroxideHCID 192733Bis(1,2-dimethylpropyl)boraneHCID 538897305,5-Dimethyl-3-tetrahydropyranyloxy-1-octyneHCID 86732972Tetrahydrofuranacetic acid water

Produkt 1

HCID 204656065,5-Dimethyl-1-iodo-trans-octen-3-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8150DiglymeLösungsmittel

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 tetrahydrofuran-acetic acid-water as described in Example 996 gives the title compound.

Quellen und Nachweise

ORD-Eintrag
ord-8a811342731848d187c4656d4816c690
Quelldatensatz
uspto-grants-1977_02
Patentnummer
US04007210

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