Chloroform → HCID 58575621, compound

HRID 1807848Notes

Reaction equation

HRID 1807848 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(Cl)(Cl)Cl.Cl[C:17]1[CH:18]=[C:19]([CH:28]=[CH:29][C:30]=1Cl)[CH2:20]N=C([O-])C(Cl)(Cl)Cl.FC(F)(F)S(O)(=O)=O>CCCCCC>[CH2:20]([O:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:19]1[CH:28]=[CH:29][CH:30]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 62406Trifluoromethanesulfonic acidHCID 2724648rel-Ethyl (1R,2S)-2-hydroxycyclopentanecarboxylateHCID 86660663HCID 86660663, compound

Product 1

HCID 58575621HCID 58575621, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a mixture of 1.00 g of ethyl cis-2-hydroxy-1-cyclopentane carboxylate, 8.00 mL of chloroform, 16.0 mL of normal hexane, and 1.77 mL of 3,4-dichlorobenzyl-2,2,2-trichloroacetimidate was added 0.335 mL of trifluoromethane sulfonic acid at room temperature under a nitrogen atmosphere, followed by stirring for 3 hours. The insoluble materials were removed by filtration, and to the filtrate was added a saturated aqueous sodium hydrogen carbonate solution under ice-cooling to adjust the pH to about 7, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate) to obtain 1.27 g of ethyl cis-2-benzyloxy-1-cyclopentane carboxylate as a colorless oily substance.

Workup

  1. customThe insoluble materials were removed by filtration
  2. additionto the filtrate was added a saturated aqueous sodium hydrogen carbonate solution under ice-
  3. temperaturecooling
  4. extractionfollowed by extraction with chloroform
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe obtained residue was purified by silica gel column chromatography (normal hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e82a2cd911f84b47a463d2156543df07
Source dataset
uspto-grants-2013_01
Patent number
US08357688B2

Reaction notes

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