Hydrochloric Acid → HCID 15124024, compound

HRID 1084872Notes

Reaction equation

HRID 1084872 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([OH:23])=[C:8]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:9]=[C:10]([C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:5]=2[O:4][C:3]=1C(O)=O.N1C2C(=CC=CC=2)C=CC=1.Cl>[Cu].C(OCC)(=O)C>[CH3:1][C:2]1[C:6]2[C:7]([OH:23])=[C:8]([C:19]([CH3:21])([CH3:20])[CH3:22])[CH:9]=[C:10]([C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:5]=2[O:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7047QuinolineHCID 15124023HCID 15124023, compound

Product 1

HCID 15124024HCID 15124024, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
195 °C

Procedure

A mixture of 3-methyl-4-hydroxy-5-t-butyl-7-benzoylbenzofuran-2-carboxylic acid (0.334 g, 0.98 mmol), quinoline (1 mL), and copper powder (0.062 g, 0.98 mmol) was warmed to 195° C. until gas evolution had ceased (about 10 minutes). The reaction mixture was allowed to cool and poured into 2N HCl (40 mL). Ethyl acetate (25 mL) was added and the biphasic mixture was filtered through a pad of celite. The layers were separated and the aqueous layer extracted with ethyl acetate (25 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Flash chromatography using 10% ethyl acetate in hexane as eluant afforded 3-methyl-4-hydroxy-5-tert-butyl-7-benzoylbenzofuran, compound 16 as a white solid after trituration from hexane. 1H NMR d 1.49 (9H, s), 2.51 (3H, d, J=2 Hz), 5.78 (1H, s), 7.31 (1H, s), 7.54 (3H, m), 7.66 (1H, s), 7.85 (2H, m).

Workup

  1. custom(about 10 minutes)
  2. temperatureto cool
  3. filtrationthe biphasic mixture was filtered through a pad of celite
  4. customThe layers were separated
  5. extractionthe aqueous layer extracted with ethyl acetate (25 mL)
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-df97223cdda241ec8843df1c2ea83da7
Source dataset
uspto-grants-1991_04
Patent number
US05006549

Reaction notes

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