Hydrochloric Acid → HCID 136340737, compound

HRID 1870506Notes

Reaction equation

HRID 1870506 reaction equation
[CH2:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[O:17]COC)=[C:8](/[CH:21]=[C:22](\[CH2:28][C:29]2[C:37]([O:38][CH3:39])=[CH:36][C:32]3[CH2:33][CH2:34][O:35][C:31]=3[CH:30]=2)/[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:7]=[N:6]1)[CH2:2][CH2:3][CH3:4].Cl>CCO>[CH2:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[OH:17])=[C:8](/[CH:21]=[C:22](\[CH2:28][C:29]2[C:37]([O:38][CH3:39])=[CH:36][C:32]3[CH2:33][CH2:34][O:35][C:31]=3[CH:30]=2)/[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:7]=[N:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11827800HCID 11827800, compound

Product 1

HCID 136340737HCID 136340737, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Ethyl (E)-3-[1-n-butyl-5-(4-chloro-2-methoxymethoxyphenyl)-1H-pyrazol-4-yl]-2-[(5-methoxy-2,3-dihydrobenzofuran-6-yl)methyl]-2-propenoate (4.50 g, 8.10 mmol) in EtOH (60 mL) was added 0.6 mL of conc. HCl. After heating at reflux for 3 h, the mixture was concentrated and then diluted with EtOAc. The resulting mixture was washed with 5% NaHCO3, brine and dried (Na2SO4). After removing the solvent, column chromatography of the residue with 25% EtOAc in hexane gave 2.65 g (64%) of the title compound as a solid: m.p. 158-160° C.; MS (ESI) m/z 511 (M+H)+ ; 1H NMR (400 MHz, CDCl3) d 7.58 (s, 1 H), 7.47 (s, 1 H), 7.02 (d, 1 H), 6.78 (s, 1 H), 6.62 (dd, 1 H), 6.59 (d, 1 H), 6.48 (s, 2 H), 5.50 (bs, 1 H), 4.48 (t, 2 H), 4.12 (m, 2 H), 3.85-3.95 (m, 4 H), 3.83 (s, 3 H), 3.81 (s, 3 H), 3.16 (t, 2 H), 1.67 (m, 2 H), 1.20 (t, 3 H), 1.17 (m, 2 H), 0.80 (t, 3 H).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 3 h
  3. concentrationthe mixture was concentrated
  4. additiondiluted with EtOAc
  5. washThe resulting mixture was washed with 5% NaHCO3, brine
  6. dry with materialdried (Na2SO4)
  7. customAfter removing the solvent, column chromatography of the residue with 25% EtOAc in hexane

Sources & evidence

ORD record
ord-5df48818d77249afaa3932eb376770b0
Source dataset
uspto-grants-2000_08
Patent number
US06096897

Reaction notes

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