Hydrochloric Acid → HCID 86753622, compound

HRID 343576Notes

Reaction equation

HRID 343576 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3(/[CH:25]=[CH:26]/[C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([C:33]#[N: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>O1CCCC1>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3(/[CH:25]=[CH:26]/[C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([C:33]#[N:34])[CH:28]=4)[CH2:16][CH2:17][C:18](=[O:21])[CH2:19][CH2:20]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 70072659HCID 70072659, compound

Product 1

HCID 86753622HCID 86753622, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

A solution of crude 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-(2[E]-(3-cyanophenyl)ethenyl)-1,1-(ethylenedioxy)cyclohexane (0.58 g, 1.06 mmol) in tetrahydrofuran (20 mL) was treated with 3N aqueous hydrochloric acid (2.3 mL) under argon and heated at 75°-80° C. for 1 h. Additional hydrochloric acid (13 mL) was then added and the mixture heated at 75° C. for another 15 min. The reaction mixture was concentrated in vacuo, was extracted into methylene chloride, and the organic extract was washed with water, dilute sodium bicarbonate solution, brine, and was dried (sodium sulfate). Purification by chromatography (silica, 1 to 2% ethyl acetate in methylene chloride) and crystallization from ethyl ether gave the tided compound as a white solid (0.329 g, 74%). mp 116°-117° C. Anal. (C27H29NO3.1/6H2O) calcd: C 77.48, H 7.06, N 3.35, found: C 77.63, H 6.94, N 3.33. 1H-NMR (400 MHz, CDCl3) δ 7.60 (s, 1H), 7.55-7.45 (m, 2H), 7.39 (t, J=7.7 Hz, 1H), 6.97 (dd, J=2.4 Hz, J=8.5 Hz, 1H), 6.89 (d, J=8.4 Hz, 1H), 6.37 (d, J=16.1 Hz, 1H), 6.22 (d, J=16.2 Hz, 1H), 4.77 (p, J=4.5 Hz, 1H), 3.86 (s, 3H), 2.6-1.5 (m, 18H with H2O).

Workup

  1. temperatureheated at 75°-80° C. for 1 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. extractionwas extracted into methylene chloride
  4. extractionthe organic extract
  5. washwas washed with water, dilute sodium bicarbonate solution, brine
  6. dry with materialwas dried (sodium sulfate)
  7. customPurification
  8. customby chromatography (silica, 1 to 2% ethyl acetate in methylene chloride) and crystallization from ethyl ether

Sources & evidence

ORD record
ord-05453d2097d042deb9abcb69f3e4c6f6
Source dataset
uspto-grants-1999_01
Patent number
US05861421

Reaction notes

Loading…