Tetrahydrofuran → HCID 20071765, compound

HRID 981251Notes

Reaction equation

HRID 981251 reaction equation
[C:1]([C:4]1[CH:28]=[CH:27][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([OH:26])[CH:20]([CH3:25])[CH2:21][C:22]([OH:24])=[O:23])=[CH:15][CH:14]=2)=[C:6]([CH2:29][CH2:30][CH3:31])[C:5]=1[OH:32])(=[O:3])[CH3:2].[OH-].[Na+].[CH2:35]1COCC1>CO>[C:1]([C:4]1[CH:28]=[CH:27][C:7]([O:8][CH2:9][CH2:10][CH2:11][S:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([OH:26])[CH:20]([CH3:25])[CH2:21][C:22]([O:24][CH3:35])=[O:23])=[CH:15][CH:14]=2)=[C:6]([CH2:29][CH2:30][CH3:31])[C:5]=1[OH:32])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 180600HCID 180600, compound

Product 1

HCID 20071765HCID 20071765, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To the 4-((3-(4-acetyl-3-hydroxy-2-propylphenoxy) propyl)thio)-beta-methyl-gamma-hydroxybenzene butanoic acid γlactone (8.84 g, 20 mM) described in EP 104,885 (Apr. 4, 1984) was added a mixture of 2N NaOH (12 ml, 24 mM), THF (50 ml) and MeOH (20 ml) and the mixture was stirred 12 hours under N2. The reaction mixture was evaporated to dryness and dissolved in water (75 ml) and cooled to 0° C.; 1N HCl was added drop wise until the PH was lower than 6 and the organic compound was extracted into EtOAc (200 ml). The organic layer was washed with brine (100 ml) and dried with Na2SO4. The solvent was removed in vacuo with no heating and the residue was dissolved in Et2O (100 ml) and cooled to 0° C. Diazomethane (in Et2O) was added in excess and the reaction mixture was evaporated to dryness with no heat and dried under high vacuum to yield the title compound as an oil slightly contaminated (by less than 10 percent of the starting lactone).

Workup

  1. additionwas added
  2. customThe reaction mixture was evaporated to dryness
  3. dissolutiondissolved in water (75 ml)
  4. addition1N HCl was added drop wise until the PH
  5. extractionthe organic compound was extracted into EtOAc (200 ml)
  6. washThe organic layer was washed with brine (100 ml)
  7. dry with materialdried with Na2SO4
  8. customThe solvent was removed in vacuo with no heating and the residue
  9. dissolutionwas dissolved in Et2O (100 ml)
  10. temperaturecooled to 0° C
  11. additionDiazomethane (in Et2O) was added in excess and the reaction mixture
  12. customwas evaporated to dryness with
  13. temperatureno heat
  14. customdried under high vacuum

Sources & evidence

ORD record
ord-5052b99b80d64feca334dd9a1f2a7251
Source dataset
uspto-grants-1991_02
Patent number
US04990526

Reaction notes

Loading…