Hydrochloric Acid → HCID 54569902, compound

HRID 2399343Notes

Reaction equation

HRID 2399343 reaction equation
[OH-].[Na+].[C:3]([CH2:7][CH:8]1[CH2:12][CH:11]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[Cl:26])[O:10][C:9]1=[O:27])([O:5]C)=[O:4].Cl>CO>[C:3]([CH2:7][C@H:8]1[CH2:12][C@@H:11]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[Cl:26])[O:10][C:9]1=[O:27])([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19387349HCID 19387349, compound

Product 1

HCID 54569902HCID 54569902, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous NaOH (1M, 1.43 ml, 1.43 mmol) was added slowly to a stirred solution of the diastereoisomers of ±3-(carbomethoxymethyl)-5-[6-(2,4-dichlorophenyl)hexyl]tetrahydrofuran-2-one (185 mg, 0. 478 mmol) in methanol (5 ml) at 0° C. After 5 min at 0° C., the mixture was stirred at room temperature for 6 h, then poured into aqueous HCl and extracted with ether. The solvent was removed under vacuum and the residue heated at 60° C. in a 1:1 mixture of 3M aqueous HCl and tetrahydrofuran for 6 h. The mixture was cooled and extracted with ether. The extracts were washed with water, saturated aqueous NaCl, and dried (MgSO4). The solvent was removed under vacuum to give an oil, which slowly crystallised. The solid was recrystallised (ether/petroleum ether 40°-60° C.) to give the title compound (126 mg, 71%), m.p. 57°-59° C.

Workup

  1. extractionextracted with ether
  2. customThe solvent was removed under vacuum
  3. temperaturethe residue heated at 60° C. in a 1:1 mixture of 3M aqueous HCl and tetrahydrofuran for 6 h
  4. temperatureThe mixture was cooled
  5. extractionextracted with ether
  6. washThe extracts were washed with water, saturated aqueous NaCl
  7. dry with materialdried (MgSO4)
  8. customThe solvent was removed under vacuum
  9. customto give an oil, which
  10. customslowly crystallised
  11. customThe solid was recrystallised (ether/petroleum ether 40°-60° C.)

Sources & evidence

ORD record
ord-993ea991684d4fa78ebffe7bb695d34f
Source dataset
uspto-grants-1995_09
Patent number
US05447954

Reaction notes

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