Ethylene Glycol → 4-Cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)cyclohexane

HRID 343542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 343542
[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)#[N:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:35](O)[CH2:36][OH:37]>C1C=CC=CC=1>[C:1]([C:3]1([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:11]=2)[CH2:8][CH2:7][C:6]2([O:37][CH2:36][CH2:35][O:9]2)[CH2:5][CH2:4]1)#[N:2]

Komponenten

5

Edukt 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 9861604SB-200473

Produkt 1

HCID 153920364-Cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)cyclohexane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A solution of 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one (1.0 g, 3.19 mmol, prepared by the procedures described in PCT applications PCT/US3/01990 (WIPO publication No. WO 93/19748) and PCT application PCT/US93/02325 published as WIPO number WO 93/19750) in benzene (25 mL) was treated with p-toluenesulfonic acid (5 mg) and ethylene glycol (0.18 mL, 3.19 mmol) and was heated to reflux under an argon atmosphere; water was removed from the mixture via a Dean-Stark trap. After 1.5 h, ether (200 mL) was added, the solution was washed with aqueous 5% sodium bicarbonate and brine, was dried (potassium carbonate) and was evaporated to provide a clear colorless oil. 1H NMR(250 MHz, CDCl3) δ 7.0 (m, 2H), 6.85 (d, J=7 Hz, 1H), 4.8 (m, 1H), 4.0 (m, 4H), 3.85 (s, 3H), 1.58-2.20 (m, 16H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux under an argon atmosphere
  3. customwater was removed from the mixture via a Dean-Stark trap
  4. additionether (200 mL) was added
  5. washthe solution was washed with aqueous 5% sodium bicarbonate and brine
  6. dry with materialwas dried (potassium carbonate)
  7. customwas evaporated
  8. customto provide a clear colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-b07c7758ae464150a99af07ce7bf92e7
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05861421

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