Ethanol → HCID 19600860, compound

HRID 609886Notes

Reaction equation

HRID 609886 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:16]2[N:20]([CH2:21][CH2:22][CH2:23]O)[C:19](=[O:25])[CH:18]([CH2:26][C:27]([OH:29])=[O:28])[S:17]2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].P(Br)(Br)[Br:31].[CH2:34](O)[CH3:35]>C(OCC)C>[C:12]([C:9]1[CH:8]=[C:7]([CH:16]2[N:20]([CH2:21][CH2:22][CH2:23][Br:31])[C:19](=[O:25])[CH:18]([CH2:26][C:27]([O:29][CH2:34][CH3:35])=[O:28])[S:17]2)[CH:6]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[C:10]=1[OH:11])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 702EthanolHCID 24614Phosphorus tribromideHCID 19600888HCID 19600888, compound

Product 1

HCID 19600860HCID 19600860, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-(3-hydroxypropyl)-5-carboxymethyl-1,3-thiazolidin-4-one (2.45 g) in diethyl ether (30 ml) was added phosphorus tribromide (3.45 g), and the mixture was stirred at room temperature for 3 hours. To the mixture was added dropwise ethanol (30 ml) under cooling with ice, the mixture was stirred at room temperature overnight. After completion of the reaction, the reaction mixture was poured into 100 ml of ice-water, and the product was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane, 20:80) and then recrystallized from chloroform/n-hexane to afford 1.50 g (51%) of the title compound as colorless crystals. mp 154-155° C. NMR (CDCl3) (200 MHz) δ: 1.26 (3H, t, J7.1 Hz), 1.43 (18H, s), 1.6-2.2 (2H, m), 2.6-3.1 (2H, m), 3.2-3.6 (4H, m), 4.17 (2H, q, J=7.1 Hz), 4.1-4.4 (1H, m), 5.33 (1H, s), 5.53 (1H, s), 7.14 (2H, s)

Workup

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred at room temperature overnight
  3. customAfter completion of the reaction
  4. extractionthe product was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed by evaporation under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate:n-hexane, 20:80)
  9. customrecrystallized from chloroform/n-hexane

Sources & evidence

ORD record
ord-5b05ad8eec0648229c1fa567db7ddf31
Source dataset
uspto-grants-1999_12
Patent number
US05998452

Reaction notes

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