Methanol → HCID 14855083, compound

HRID 704887Notes

Reaction equation

HRID 704887 reaction equation
[Na].[Cl:2][C:3]1[CH:28]=[CH:27][C:6]([C:7]([C:9]2[N:13]([CH2:14][CH2:15][CH:16]3[C:21](=[O:22])[O:20][C:19](C)(C)[O:18][C:17]3=[O:25])[C:12]([Cl:26])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.[CH3:29]O>Cl>[Cl:2][C:3]1[CH:28]=[CH:27][C:6]([C:7]([C:9]2[N:13]([CH2:14][CH2:15][CH:16]([C:21]([O:20][CH3:19])=[O:22])[C:17]([O:18][CH3:29])=[O:25])[C:12]([Cl:26])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 887Methanol2×HCID 67929239HCID 67929239, compound

Product 1

HCID 14855083HCID 14855083, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
0 °C

Procedure

The 5-(4-chlorobenzoyl)-2-chloro-1-[2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)ethyl]pyrrole sodium salt from Example 3A was dissolved in methanol saturated with hydrogen chloride (30 ml) and stirred at 0° C. for three hours. The solution was diluted with methanol (30 ml) and allowed to warm to room temperature, and was then stirred for another four hours. The solvent was then evaporated under reduced pressure at 10°-20° C. The residue was partitioned between ether and water (150 ml+150 ml), and the water was extracted with ether (2×150 ml). The combined ether extracts were dried over anhydrous sodium sulfate and evaporated to dryness. The residue was chromatographed on Florisil® (50 g/g mixture), eluting the product with hexane/ethyl acetate, 7:3. The product so obtained (1.912 g, 68%) was a colorless crystalline solid, which was recrystallized from dichloromethane/hexane to afford 5-(4-chlorobenzoyl)-2-chloro-1-[3,3-di(methoxycarbonyl)propyl]pyrrole, having the following properties:

Workup

  1. temperatureto warm to room temperature
  2. stirringwas then stirred for another four hours
  3. customThe solvent was then evaporated under reduced pressure at 10°-20° C
  4. customThe residue was partitioned between ether and water (150 ml+150 ml)
  5. extractionthe water was extracted with ether (2×150 ml)
  6. dry with materialThe combined ether extracts were dried over anhydrous sodium sulfate
  7. customevaporated to dryness
  8. customThe residue was chromatographed on Florisil® (50 g/g mixture)
  9. washeluting the product with hexane/ethyl acetate, 7:3
  10. customThe product so obtained (1.912 g, 68%)
  11. customwas recrystallized from dichloromethane/hexane

Sources & evidence

ORD record
ord-7cf2e67579dc469eb0d2c064a3cbbbd6
Source dataset
uspto-grants-1991_01
Patent number
US04988822

Reaction notes

Loading…