Isopropanol → HCID 57238292, compound

HRID 2254638Notes

Reaction equation

HRID 2254638 reaction equation
[OH:1][CH2:2][C:3](=[C:14]1[S:18][C:17](=[O:19])[NH:16][C:15]1=[O:20])[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.CC(O)C>CC(C)=O>[O:1]=[CH:2][C:3](=[C:14]1[S:18][C:17](=[O:19])[NH:16][C:15]1=[O:20])[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 57160990HCID 57160990, compoundHCID 131709961Jones' reagent

Product 1

HCID 57238292HCID 57238292, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-[2-hydroxy-1-(1-naphthalenyl)ethylidene]-2,4-thiazolidinedione (10.13 g, 35.5 mmol) in acetone (250 mL) at 0° C. was added Jones reagent (8N, 10.26 mL, 82 mmol). After 30 min 2-propanol (10 mL) was added. The reaction mixture was filtered and concentrated in vacuo. The resulting oil was taken up in ether and washed with water (2×). The organic phase was dried over magnesium sulfate, filtered and concentrated to give a foam (9.88 g). Recrystallization (chloroform/ethyl acetate) gave crystals (6.87 g) of the E-isomer. m.p. 184°-185° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. washwashed with water (2×)
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d87c7c5eab5a413dba163b83f3a7a6c9
Source dataset
uspto-grants-1993_08
Patent number
US05236941

Reaction notes

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