Iodine → HCID 53975217, compound

HRID 1581119Notes

Reaction equation

HRID 1581119 reaction equation
II.[OH:3][CH:4]1[CH2:8][CH2:7][CH:6]([CH:9]=[CH:10][CH:11]([OH:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:5]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25].[Cl-].[NH4+].I[CH2:31]I>C(OCC)C.[Cu].[Zn]>[OH:3][CH:4]1[CH2:8][CH2:7][CH:6]([CH:9]2[CH2:31][CH:10]2[CH:11]([OH:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:5]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25]

Participants

7

Reactant 4

HCID 807IodineHCID 6346DiiodomethaneHCID 25517Ammonium ChlorideHCID 54187079Methyl 7-[2-hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoate

Product 1

HCID 53975217HCID 53975217, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 10290809Zinc copper coupleCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

A suspension of zinc-copper couple (1.0 g.) (prepared by the method of R.S. Shank and H. Schechter, J. Org. Chem. (1959), 24, 1825) in diiodomethane (4.0 g.) and dry diethyl ether (10 ml.) was refluxed with a crystal of iodine for 0.5 hours. To the resulting suspension was added methyl 7-[2-hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoate (1.0 g.) [prepared as described in Example 5] in dry diethyl ether (10 ml.) and the resulting mixture was refluxed for 24 hours. Addition of saturated ammonium chloride broke up the complex formed and the remaining zinc-copper couple was removed by filtration. The filtrate was separated and the diethyl ether layer dried over magnesium sulphate and evaporated to give methyl 7-[2-hydroxy-5-(3-hydroxy-1,2-methylene-1-octyl)cyclopentyl]heptanoate (1.04 g.). This was purified by preparative thin layer chromatography using the system employed in Example 10,νmax 3400 cm-1, 1730 cm-1 and 1170 cm-1.

Workup

  1. customprepared by the method of R.S
  2. temperaturethe resulting mixture was refluxed for 24 hours
  3. customformed
  4. customthe remaining zinc-copper couple was removed by filtration
  5. customThe filtrate was separated
  6. dry with materialthe diethyl ether layer dried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-31e075f4c0094d26818624804417adf8
Source dataset
uspto-grants-1976_01
Patent number
US03935261

Reaction notes

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