Isobutylene → HCID 21566090, compound

HRID 1580335Notes

Reaction equation

HRID 1580335 reaction equation
C1CO[C:3]2([CH2:7][CH2:6][CH:5]([S:8][CH2:9][C:10]([OH:17])([CH3:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:4]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])[O:2]1.C(CCCCCCC1C(=O)CCC=1)(O)=O.OC(CCCCC)CS.CC(=C)C.C1COC2(CCC(SCC(=O)CCCCC)C2CCCCCCC(OC(C)(C)C)=O)O1.C[Mg]Br>CCOCC.C(O)CO>[C:24]([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH:4]1[CH:5]([S:8][CH2:9][C:10]([OH:17])([CH3:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:6][CH2:7][C:3]1=[O:2])([OH:26])=[O:25]

Participants

9

Reactant 6

HCID 8255IsobutyleneHCID 789025-Oxo-1-cyclopentene-1-heptanoic acidHCID 199833961-Sulfanylheptan-2-olHCID 68142961HCID 68142961, compoundHCID 68143609HCID 68143609, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 21566090HCID 21566090, compound

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 3283Diethyl EtherSolvent

Procedure

4.7 g. of 1,1-ethylenedioxy-2-(6-tert.-butoxycarbonylhexyl)-3-(2-hydroxy-2-methylheptylthio)-cyclopentane (obtainable from 2-(6-carboxyhexyl)-2-cyclopentenone, addition of 2-hydroxyheptanethiol, subsequent ketalization with ethylene glycol, as well as oxidation with CrO3 in ether, addition to isobutylene, and reaction of the thus-obtained 1,1-ethylenedioxy-2-(6-tert.-butoxycarbonylhexyl)-3-(2-oxoheptylthio)-cyclopentane with methylmagnesium bromide) is agitated for 2 hours at room temperature in 60 ml. of 2N aqueous HCl, extracted, after cooling, three times with CH2Cl2 ; the organic phase is washed with water, dried over Na2SO4, the solvent is distilled off, and chromatographic purification of the residue (silica gel/chloroform) yields 2-(6-carboxyhexyl)-3-(2-hydroxy-2-methylheptylthio)-cyclopentanone. Rf = 0.25 (silica gel/chloroform : methanol = 95 : 5).

Workup

  1. extractionof 2N aqueous HCl, extracted
  2. temperatureafter cooling
  3. washthe organic phase is washed with water
  4. dry with materialdried over Na2SO4
  5. distillationthe solvent is distilled off
  6. customchromatographic purification of the residue (silica gel/chloroform)

Sources & evidence

ORD record
ord-cd0f47e2ca2748ac873e586b3aca1706
Source dataset
uspto-grants-1976_01
Patent number
US03932487

Reaction notes

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