Methanol → HCID 54053046, compound

HRID 1600877Notes

Reaction equation

HRID 1600877 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=2[CH:17]=[C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][C:19]2=[O:27])=[CH:6][CH:5]=1)([OH:3])=[O:2].S(=O)(=O)(O)O.[CH3:33]O>>[CH3:33][O:2][C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:11]=2[CH:17]=[C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][C:19]2=[O:27])=[CH:8][CH:9]=1)=[O:3]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 54424865HCID 54424865, compound

Product 1

HCID 54053046HCID 54053046, compound

Procedure

The resultant compound 29 (22.0 g) was added to 1000 ml methanol, and the mixture was refluxed with heat for 8 hours through use of 50 ml of conc. sulfuric acid. After completion of reaction, the reaction mixture was cooled, methanol evaporated, followed by extraction with ethyl acetate. The extract was washed with water, saturated sodium bicarbonate water, and saturated brine, and subsequently dried over sodium sulfate, and then evaporated. The resultant crude product was purified by silica gel column chromatography (chloroform), to thereby obtain 5.0 g (yield 21.9%) of the E-isomer of the title compound in the form of orange-colored crystals and 16.7 g (yield 73.2%) of the Z-isomer of the title compound in the form of yellow-colored crystals. The melting point and elementary analysis data are shown in Table 11, and NMR and MS spectrum data are shown in Table 12.

Workup

  1. temperaturethe mixture was refluxed
  2. customAfter completion of reaction
  3. temperaturethe reaction mixture was cooled
  4. custommethanol evaporated
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe extract was washed with water, saturated sodium bicarbonate water, and saturated brine
  7. dry with materialsubsequently dried over sodium sulfate
  8. customevaporated
  9. customThe resultant crude product was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-e068e08a588e490f90382c1a70972332
Source dataset
uspto-grants-1999_11
Patent number
US05977130

Reaction notes

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