Hydrochloric Acid → HCID 23323867, compound

HRID 1381371Notes

Reaction equation

HRID 1381371 reaction equation
O[C:2]1[C:3](=[O:17])[O:4][CH:5]([CH2:13][CH2:14][CH2:15][OH:16])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C.[C:25](Cl)(=[O:29])[O:26][CH2:27][CH3:28].Cl>O1CCCC1>[OH:16][CH2:15][CH2:14][CH2:13][CH:5]1[O:4][C:3](=[O:17])[C:2]([C:25]([O:26][CH2:27][CH3:28])=[O:29])=[C:6]1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 133895803-Hydroxy-5-(3-hydroxypropyl)-4-phenylfuran-2(5H)-one

Product 1

HCID 23323867HCID 23323867, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Hydroxy-5-(3-hydroxypropyl)-4-phenyl-2(5H)-furanone (25 mg) was dissolved in tetrahydrofuran (6 ml), and triethylamine (0.018 ml) was added with ice-cooling and stirring, followed by dropwise addition of ethyl chlorocarbonate (0.012 ml). The mixture was stirred at the same temperature for 5 minutes, and the reaction mixture was acidified with hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate. The solvent was then distilled off. The remaining oil was purified by preparative thin layer chromatography (silica gel; developer: 4% methanol-chloroform) to give ethyl 5-(3-hydroxypropyl)-2-oxo-4-phenyl-2,5-dihydro-3-furancarboxylate (30 mg) as a colorless oil.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at the same temperature for 5 minutes
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was then distilled off
  7. customThe remaining oil was purified by preparative thin layer chromatography (silica gel; developer: 4% methanol-chloroform)

Sources & evidence

ORD record
ord-15c1ffb5f7aa4ad18db14bf8bf71192b
Source dataset
uspto-grants-1986_04
Patent number
US04585789

Reaction notes

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