Hydrochloric Acid → 1-(3-Methylthio-4-propoxy-5-benzyloxyphenyl)4-(3,4,5-trimethoxyphenyl)butan-1,4-dione

HRID 1110821Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1110821
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]=1[O:11][CH2:12][CH2:13][CH3:14])[CH:6]=[O:7].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:35]=[CH:36][C:37](C=CC2C=C(OC)C(OC)=C(OC)C=2)=O)[CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32].C(N(CC)CC)C.Cl.CN(C)C=[O:64]>[Br-].C([N+]1C(C)=C(CCO)SC=1)C>[CH3:1][S:2][C:3]1[CH:4]=[C:5]([C:6](=[O:7])[CH2:37][CH2:36][C:35]([C:27]2[CH:26]=[C:25]([O:24][CH3:23])[C:30]([O:31][CH3:32])=[C:29]([O:33][CH3:34])[CH:28]=2)=[O:64])[CH:8]=[C:9]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]=1[O:11][CH2:12][CH2:13][CH3:14]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8471TriethylamineHCID 3834051,5-Bis(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-oneHCID 104710223-Methylthio4-n-propoxy-5-benzyloxybenzaldehyde

Produkt 1

HCID 100987431-(3-Methylthio-4-propoxy-5-benzyloxyphenyl)4-(3,4,5-trimethoxyphenyl)butan-1,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 99649233-Ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromideKatalysator

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

3-methylthio-4-n-propoxy-5-benzyloxybenzaldehyde, 135 g of 3,4,5-trimethoxyphenylvinylketone, 10 g of 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazoliumbromide, 25 mL of triethyl amine dissolved in 150 ml of dimethylformamide was heated at 60° C. overnight, and the reaction mixture was treated with 400 mL of 1.5N HCl and the aqueous layer decanted. The residue was treated again with fresh 400 mL of 1.5N HCl and decanted two more times. The remaining residue was crystallized from 400 mL of methanol and washed thoroughly with methanol, hexane, and methanol and dried to yield the title compound as a tan solid: NMR(200 MHz, CDCl3) δ 1.03(t, CH2CH2CH3), 1.82(m, CH2CH2CH3), 2.50(s, SCH3), 3.43(s, C(O)CH2CH2CO, 3.94(s, 3 OCH3), 4.11 (t, OCH2CH2CH3), 5.17(s, OCH2Ar), 7.30-7.52(m, ArH).

Aufarbeitung

  1. customthe aqueous layer decanted
  2. additionThe residue was treated again with fresh 400 mL of 1.5N HCl
  3. customdecanted two more times
  4. customThe remaining residue was crystallized from 400 mL of methanol
  5. washwashed thoroughly with methanol, hexane, and methanol
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5cac2286850a4cea96c3e94dde8153df
Quelldatensatz
uspto-grants-1990_12
Patentnummer
US04977146

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