Iodocyclopentane → HCID 68867447, compound

HRID 1985255Notes

Reaction equation

HRID 1985255 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([OH:20])[C:17]([OH:19])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:21]1(I)[CH2:25][CH2:24][CH2:23][CH2:22]1>CN(C=O)C.CCOCC.[Ag-]=O>[CH:21]1([O:18][C:17](=[O:19])[CH:16]([O:20][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)[CH2:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:10][CH:11]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 2

HCID 73784IodocyclopentaneHCID 10707314141109-82-2

Product 1

HCID 68867447HCID 68867447, compoundYield 17%

Reagents, catalysts & solvents 3

HCID 178418778HCID 178418778, compoundCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 3-(4-benzyloxy-phenyl)-2-hydroxy-propionic acid (1.0 g, 3.67 mmol), cyclopentyl iodide (7.2 g, 36.7 mmol) and silver (I) oxide (4.25 g, 18.3 mmol) in DMF (15 mL) was heated at 55° C. under N2 for 72 h. The reaction mixture was cooled, diluted with Et2O and filtered through hyflo. The filtrate was extracted with water and the organic layer was dried (MgSO4) and the solvent removed in vacuo to afford crude product that was purified by flash chromatography using 10:1 hexanes:acetone to afford 0.255 g (17%) 3-(4-benzyloxy-phenyl)-2-cyclopentyloxy-propionic acid cyclopentyl ester. Rf=0.67 (1:1 hexanes:acetone). 1H NMR.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered through hyflo
  3. extractionThe filtrate was extracted with water
  4. dry with materialthe organic layer was dried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto afford crude product that
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-21d895c7c1ab4a718e72efbebd2d4779
Source dataset
uspto-grants-2009_06
Patent number
US07544812B2

Reaction notes

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