Hydrochloric Acid → HCID 18454846, compound

HRID 1271660Notes

Reaction equation

HRID 1271660 reaction equation
Br[CH:2]([C:18]([OH:20])=[O:19])[CH2:3][CH2:4][C:5]1[CH:17]=[CH:16][C:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:7][CH:6]=1.[C:21]([O-:24])(=[S:23])[CH3:22].[K+].Cl.CCOC(C)=O.CC(O)=O>[OH-].[Na+]>[C:21]([S:23][CH:2]([C:18]([OH:20])=[O:19])[CH2:3][CH2:4][C:5]1[CH:17]=[CH:16][C:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:7][CH:6]=1)(=[O:24])[CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 18454847HCID 18454847, compoundHCID 22609514Ethyl acetate acetateHCID 23670855Potassium ethanethioate

Product 1

HCID 18454846HCID 18454846, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 0.125 g (0.36 mM) of the ester obtained in step 1 in 0.364 ml of 1 N sodium hydroxide is cooled to 0° C. 0.05 g (1.2 eq) of potassium thioacetate is added and the mixture is stirred at room temperature for 48 hours. The resulting mixture is acidified to 0° C. with 1N hydrochloric acid solution. It is extracted with ethyl acetate and the organic phase is washed with water and with saturated sodium chloride solution. After drying and evaporation, a colorless oil is obtained. (Mass: 0.12 g, 98%). Rf (c.Hex/EtOAc/AcOH: 7/3/0.5)=0.11.

Workup

  1. extractionIt is extracted with ethyl acetate
  2. washthe organic phase is washed with water and with saturated sodium chloride solution
  3. customAfter drying
  4. customevaporation
  5. customa colorless oil is obtained

Sources & evidence

ORD record
ord-50b652d609e14f4c974ae7ae487540d5
Source dataset
uspto-grants-2007_04
Patent number
US07205435B2

Reaction notes

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