Sulfuric Acid → HCID 54005197, compound

HRID 327982Notes

Reaction equation

HRID 327982 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:14])[CH:10]=[CH:9][C:8]=1[O:27]C)[CH3:2].Cl.N1C=CC=CC=1.S(=O)(=O)(O)O.S(Cl)(Cl)=O>C(O)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:14])[CH:10]=[CH:9][C:8]=1[OH:27])[CH3:2]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 24386Thionyl ChlorideHCID 10176127Pyridinium chlorideHCID 54258721HCID 54258721, compound

Product 1

HCID 54005197HCID 54005197, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1.07 g (2.69 mmol) of 5-[[2-(2-ethoxy-2-oxoethyl)phenyl]carbonyl]-2-methoxybenzenepropanoic acid ethyl ester and 3.63 g (31.41 mmol) of pyridine hydrochloride was heated at 220°-260° C. for 40 min and then cooled to room temperature. Aqueous 3N sulfuric acid (40 mL) was added, and the mixture was worked-up with ethyl acetate in the usual manner. The crude product was dissolved in 150 mL of ethanol. To this solution was added 3 mL of thionyl chloride and the resulting solution was heated at reflux for 16 hr. The solvent was removed in vacuo and the crude product was purified by flash chromatography on 120 g of silica gel, eluting with 3:1 hexane-ethyl acetate. This afforded 0.469 g (45.4%) of the title compound as a pale yellow oil.

Workup

  1. temperaturewas heated at 220°-260° C. for 40 min
  2. temperaturethe resulting solution was heated
  3. temperatureat reflux for 16 hr
  4. customThe solvent was removed in vacuo
  5. customthe crude product was purified by flash chromatography on 120 g of silica gel
  6. washeluting with 3:1 hexane-ethyl acetate

Sources & evidence

ORD record
ord-531b3a0cbfe848e8a4e4b7744d38f375
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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