Hydrochloric Acid → 4-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(3-carbomethoxyphenylethynyl)cyclohexan-1-one

HRID 343553Notes

Reaction equation

HRID 343553 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]([O:35][CH3:36])=[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>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]([O:35][CH3:36])=[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 153920314-(3-Cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-(3-carbomethoxyphenylethynyl)cyclohexane

Product 1

HCID 153920324-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(3-carbomethoxyphenylethynyl)cyclohexan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-(3-carbomethoxyphenylethynyl)cyclohexane (0.060 g, 0.12 mmol) in tetrahydrofuran (5 mL) containing 3N hydrochloric acid (0.60 mL) under an argon atmosphere was heated at 55°-60° C. for 2 h. The cooled reaction mixture was partitioned between ice cold dilute aqueous sodium carbonate solution and ethyl acetate. The organic phase was washed with water, saturated brine, was dried over sodium sulfate, and was concentrated in vacuo. The residue was chromatographed (silica gel), eluting with 15% ethyl acetate/hexanes, to afford a resin. Anal. (C28H30O5.1/4 H2O) calcd: C 74.56, H 6.82, found: C 74.43, H 6.80. 1H-NMR (400 MHz, CDCl3) δ 8.15 (s, 1H), 8.00 (d-d, J=1.5 Hz;J=6.6 Hz, 1H), 7.65 (d-d, J=1.3 Hz, J=7.7 Hz, 1H), 7.43 (t, J=7.7 Hz, 1H), 7.21 (d, J=2.1, 1H), 7.12 (d-d, J=2.0 Hz, J=8.5 Hz, 1H), 6.87 (d, J=8.5 Hz,1H), 4.81 (m, 1H), 3.94 (s, 3H), 3.86 (s, 3H), 3.04 (d-t, J=6.0 Hz, J=14.2, 2H), 2.50 (d,br, J=14.8, 2H), 2.4-2.2 (m, 4H), 2.0-1.5 (m).

Workup

  1. temperaturewas heated at 55°-60° C. for 2 h
  2. customThe cooled reaction mixture
  3. customwas partitioned between ice cold dilute aqueous sodium carbonate solution and ethyl acetate
  4. washThe organic phase was washed with water, saturated brine
  5. dry with materialwas dried over sodium sulfate
  6. concentrationwas concentrated in vacuo
  7. customThe residue was chromatographed (silica gel)
  8. washeluting with 15% ethyl acetate/hexanes
  9. customto afford a resin

Sources & evidence

ORD record
ord-b666d92b3dfd4333871363886a70e32f
Source dataset
uspto-grants-1999_01
Patent number
US05861421

Reaction notes

Loading…