Hydrochloric Acid → HCID 12932808, compound

HRID 2291639Notes

Reaction equation

HRID 2291639 reaction equation
[O:1]=[C:2]1[CH:6]([C:7]([O-:9])=[O:8])[CH:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4][O:3]1.Cl>C(O)C.[OH-].[Na+]>[O:1]=[C:2]1[CH:6]([C:7]([OH:9])=[O:8])[CH:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:4][O:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86742667HCID 86742667, compound

Product 1

HCID 12932808HCID 12932808, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of ethyl (4R*,5R*)-5-[3-t-butyldiphenylsilyloxy)propyl]-2-oxo-4-phenyltetrahydro-3furancarboxylate (2.43 g) in ethanol (40 ml) and 1N aqueous sodium hydroxide (9.16 ml) was stirred at 50° C. for 2 hours. 1N HYdrochloric acid (10 ml) was added to the reaction mixture and the organic solvent was evaporated in vacuo. The aqueous solution was extracted with ethyl acetate, and the'extract was washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo to give (4R*,5R*)-5-[3-t-butyldiphenylsilyloxy)propyl]-2-oxo-4-phenyltetrahydrofuran-3-carboxylic acid (2.20 g) as an oil.

Workup

  1. customthe organic solvent was evaporated in vacuo
  2. extractionThe aqueous solution was extracted with ethyl acetate, and the'extract
  3. washwas washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-e9ae3768937b4a37a49eed6dcc2a745c
Source dataset
uspto-grants-1989_01
Patent number
US04797417

Reaction notes

Loading…