Hydrochloric Acid → HCID 136364606, compound

HRID 1650816Notes

Reaction equation

HRID 1650816 reaction equation
[CH2:1]([O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([S:23][CH2:24][C:25]([O:27]CC)=O)=[O:22])=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].CC(C)([O-])C.[K+].Cl>C1COCC1.CN(C=O)C>[OH:27][C:25]1[CH2:24][S:23][C:21](=[O:22])[C:20]=1[C:17]1[CH:18]=[CH:19][C:14]([O:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 54566585HCID 54566585, compound

Product 1

HCID 136364606HCID 136364606, compoundYield 0.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a mixture of THF (50 ml) and DMF (10 ml) was dissolved ethyl S-(4-dodecyloxyphenyl)acetylthioglycolate (2.8 g, 6.6 m mol). To the solution was added at room temperature potassium tertiary butoxide (1.1 g, 10 m mol). The solution was stirred for one hour, to which was then added 2N HCl (20 ml), followed by extraction with ethyl acetate. The organic layer was washed with water, dried and concentrated under reduced pressure. The residue was purified by silica gel chromatography (developing solvent: ethyl acetate). The crude crystals obtained were recrystallized from IPE to obtain 2,5-dihydro-4-hydroxy-3-(4-dodecyloxyphenyl)thiophen-2-one (5-h, 13 mg, 0.5%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (developing solvent: ethyl acetate)
  6. customThe crude crystals obtained
  7. customwere recrystallized from IPE

Sources & evidence

ORD record
ord-26a99fd757e642d192a73b55c8a852fa
Source dataset
uspto-grants-1990_05
Patent number
US04925868

Reaction notes

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