Iodine → HCID 20442063, compound

HRID 224560Notes

Reaction equation

HRID 224560 reaction equation
C([Sn](CCCC)(CCCC)/[CH:6]=[CH:7]/[CH2:8][CH:9]([O:14][Si:15]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][CH3:17])[CH2:10][CH2:11][CH2:12][CH3:13])CCC.[I:30]I>CCOCC>[I:30]/[CH:6]=[CH:7]/[CH2:8][CH:9]([O:14][Si:15]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][CH3:17])[CH2:10][CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 807Iodine4×HCID 20442099HCID 20442099, compound

Product 1

HCID 20442063HCID 20442063, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of E-1-tri-n-butystannyl-4-triethylsilyloxy-1-octene (11 g) in 200 ml ether is added 0.9 equivalents of iodine in one portion. After 25 minutes the color of the iodine has disappeared. An additional 0.1 equivalents of iodine is added in portions until the iodine color persists. The ether is removed in vacuo to provide (E)-1-iodo-4-triethylsilyloxy-1-octene. This residue is placed on a silica-gel column (240 g SilicAR CC-7) packed in hexane. A liter fraction of hexane contains 7.5 g of mostly tri-n-butyliodostannane. A 500 ml elution of benzene gives only a small amount of material. An elution with 600 ml of ether provides 7.0 g of 1-iodo-4-hydroxy-1-octene as an oil.

Workup

  1. customThe ether is removed in vacuo

Sources & evidence

ORD record
ord-77e362c3e6174ec4ad68607732740c78
Source dataset
uspto-grants-1980_11
Patent number
US04233231

Reaction notes

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