Hydrochloric Acid → HCID 18945455, compound

HRID 399805Notes

Reaction equation

HRID 399805 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([C:16]([O:18]C)=O)[CH:9]=[C:10]([CH:15]=2)[C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:4][CH:3]=[CH:2]1.[C:20]([O:23][CH3:24])(=[O:22])[CH3:21].C[O-].[Na+].Cl>CN(C)C=O.O>[CH3:14][O:13][C:11]([C:10]1[CH:9]=[C:8]([C:16](=[O:18])[CH2:21][C:20]([O:23][CH3:24])=[O:22])[CH:7]=[C:6]([N:1]2[CH:2]=[CH:3][CH:4]=[CH:5]2)[CH:15]=1)=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6584Methyl AcetateHCID 10942334Sodium MethoxideHCID 189451711,3-Dimethyl 5-(1H-pyrrol-1-yl)-1,3-benzenedicarboxylate

Product 1

HCID 18945455HCID 18945455, compoundYield 8.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of dimethyl 5-(pyrrol-1-yl)isophthalate (3.0 g), methyl acetate (0.86 g) and sodium methoxide (0.81 g) in N,N-dimethylformamide (21 ml) was heated at 55° C. for 3 hours. After being cooled to room temperature, the reaction mixture was poured into water (100 ml) and the whole was adjusted to pH 3 with 10% hydrochloric acid. The resulting precipitate was collected and washed with water. This crude product was purified by column chromatography on silica gel (150 ml) with benzene-ethyl acetate (30:1) as an eluent. The fractions containing the object product were collected and evaporated in vacuo. The residue was recrystallized from methanol to afford methyl 3-[3-methoxycarbonyl-5-(pyrrol-1-yl)phenyl]-3-oxopropionate (0.31 g).

Workup

  1. temperatureAfter being cooled to room temperature
  2. customThe resulting precipitate was collected
  3. washwashed with water
  4. customThis crude product was purified by column chromatography on silica gel (150 ml) with benzene-ethyl acetate (30:1) as an eluent
  5. additionThe fractions containing the object product
  6. customwere collected
  7. customevaporated in vacuo
  8. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-c86ecc70f8e0455099cadca9e604dbaf
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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