Hydrochloric Acid → HCID 15392033, compound

HRID 343554Notes

Reaction equation

HRID 343554 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:25]#[C:26][C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([OH:35])=[O:34])[CH:28]=4)[CH2:20][CH2:19][C:18]4(OCC[O:21]4)[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.O.CO>O1CCCC1>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:25]#[C:26][C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([OH:35])=[O:34])[CH:28]=4)[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 54323923HCID 54323923, compound

Product 1

HCID 15392033HCID 15392033, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-(3-carboxyphenylethynyl)cyclohexane (0.11 g, 0.23 mmol) in tetrahydrofuran (6 mL) containing 3N hydrochloric acid (0.7 mL) was heated under an argon atmosphere at 55°-70° C. for 2 h. The cooled reaction mixture was concentrated in vacuo and the residue was partitioned between cold water and methylene chloride. The organic phase was washed with saturated brine solution, was dried over magnesium sulfate and was evaporated. The residue was chromatographed (silica), eluting with methylene chloride/methanol/water (90/5/0.25 to 90/10/0.5) and was concentrated in vacuo. The residue was dissolved in methanol and was foamed in vacua to afford a white fractured glass. Anal. (C27H28O5.1/4 H2O.1/4 CH3OH) calcd: C 73.55, H 6.68, found: C 73.51, H 6.66. 1H-NMR (400 MHz, CDCl3) δ 8.22 (t, J=1.5 Hz, 1H), 8.09 (d-d, J=1.3 Hz;J=7.9 Hz, 1H), 7.72 (d-d, J=1.3 Hz, J=7.8 Hz, 1H), 7.47 (t, J=7.8 Hz, 1H), 7.22 (d, J=2.2, 1H), 7.13 (d-d, J=2.3 Hz, J=8.4 Hz, 1H), 6.88 (d, J=8.5 Hz,1H), 4.82 (p, 1H), 3.86 (s, 3H), 3.25 (d, J=20 Hz, CH3OH, 0.55H), 3.04 (d-t, J=5.8 Hz, J=14.5, 1.7H), 2.50 (d,br, J=14.8, 1.8H), 2.4-2.2 (m, 4H), 2.0-1.5 (m).

Workup

  1. temperaturewas heated under an argon atmosphere at 55°-70° C. for 2 h
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated in vacuo
  4. customthe residue was partitioned between cold water and methylene chloride
  5. washThe organic phase was washed with saturated brine solution
  6. dry with materialwas dried over magnesium sulfate
  7. customwas evaporated
  8. customThe residue was chromatographed (silica)
  9. washeluting with methylene chloride/methanol/water (90/5/0.25 to 90/10/0.5)
  10. concentrationwas concentrated in vacuo
  11. dissolutionThe residue was dissolved in methanol
  12. customto afford a white fractured glass

Sources & evidence

ORD record
ord-2eeb88201b15408fa2606dba4f9507a1
Source dataset
uspto-grants-1999_01
Patent number
US05861421

Reaction notes

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