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

HRID 1112695Notes

Reaction equation

HRID 1112695 reaction equation
[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]

Participants

8

Reactant 6

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

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.

Sources & evidence

ORD record
ord-744a608a2d584252944ec6196b97cee6
Source dataset
uspto-grants-1978_10
Patent number
US04123456

Reaction notes

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