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

HRID 225362

Reaction equation

HRID 225362 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 154) successively with 233 mg. of 0.43M disiamylborane in diglyme, 22.5 g. of trimethylamine oxide, 150 ml. of 1N sodium hydroxide, 25.4 g. of iodine, and 900 ml. of 3:1:1 tetrahydrofuran-acetic acid-water as described in Example 151 gives the title compound.

Sources & evidence

ORD record
ord-659265b1752e4f169bc2cc6c9755395b
Source dataset
uspto-grants-1980_11
Patent number
US04236027

Linked notes

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