Hydrochloric Acid → (Z)-5-fluoro-2-methyl-1-(3,4,5-trimethoxybenzylidene)-3-indenylacetic acid

HRID 1954319Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1954319
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C:6]([CH3:11])=[C:5]2[CH2:12][C:13]([OH:15])=[O:14].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([O:28][CH3:29])[C:25]=1[O:26][CH3:27])[CH:21]=O.C[O-].[Na+].Cl>CO>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:21]\[C:20]1[CH:23]=[C:24]([O:28][CH3:29])[C:25]([O:26][CH3:27])=[C:18]([O:17][CH3:16])[CH:19]=1)/[C:6]([CH3:11])=[C:5]2[CH2:12][C:13]([OH:15])=[O:14]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 68583,4,5-TrimethoxybenzaldehydeHCID 30156085-Fluoro-2-methyl-1H-indene-3-acetic acidHCID 10942334Sodium Methoxide

Produkt 1

HCID 9864863(Z)-5-fluoro-2-methyl-1-(3,4,5-trimethoxybenzylidene)-3-indenylacetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

5-fluoro-2-methyl-3-indenylacetic acid (15 g, 0.072 mol), 3,4,5-trimethoxybenzaldehyde (17.85 g, 0.091 mol) and sodium methoxide (13.0 g, 0.24 mol) are heated in methanol (200 ml) at 60° C. under nitrogen with stirring for 6 hours. After cooling, the reaction mixture is poured into 750 ml of ice-water, and is acidified with 2.5 N hydrochloric acid. The collected solid is triturated with a little ether to produce (Z)-5-fluoro-2-methyl-1-(3,4,5-trimethoxybenzylidene)-3-indenylacetic acid (m.p. 166-169° C.). (R=H, R1 =H, R2 =F, R3 =H, R4 =H, R5 =OCH3, P6 =OCH3, R7 =OCH3, R8 =CH3, R9 =H, R10 and R11 =double bond, m=0, n=0, M=OH)

Aufarbeitung

  1. temperatureAfter cooling
  2. customThe collected solid is triturated with a little ether

Quellen und Nachweise

ORD-Eintrag
ord-3f0b1674d56f4f518da4aa831ecc8402
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06121321

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