Methyl iodide → 2'-(2-Methoxyethoxymethoxy)-[1,1';3',1"]terphenyl-5'-carboxylic acid methyl ester

HRID 1871290Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1871290
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][C:11]([C:20]([OH:22])=[O:21])=[CH:10][C:9]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.N12CCCN=C1CCCC[CH2:30]2.IC>C1COCC1>[CH3:30][O:21][C:20]([C:11]1[CH:10]=[C:9]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:8]([O:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])=[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=1)=[O:22]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 234456652'-(2-Methoxyethoxymethoxy)-[1,1';3',1"]terphenyl-5'-carboxylic acid

Produkt 1

HCID 541817672'-(2-Methoxyethoxymethoxy)-[1,1';3',1"]terphenyl-5'-carboxylic acid methyl esterAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

At 0° C., to a stirred solution of 2'-(2-methoxyethoxymethoxy)-[1,1';3',1"]terphenyl-5'-carboxylic acid (1.72 g, 4.55 mmol) in THF (4.55 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene. After 0.5 h, to the reaction was added iodomethane and the reaction was stirred for 16 h, eventually warming to ambient temperature. The reaction was filtered and the filtrate concentrated. The crude product was dissolved in EtOAc, washed sequentially with sat. aq. NaHCO3 (3×), with 1 N HCl (3×), brine (3×), dried (K2CO3) and concentrated. Purification on Biotage KP-Sil eluting with 20% acetone/hexane gave 1.641 g (92%) of the title compound as a yellow oil. 1H NMR (DMSO-d6) δ 2.77-2.80 (m, 2 H), 2.88-2.91 (m, 2 H), 3.01 (s, 3 H), 3.87 (s, 3 H), 4.40 (s, 2 H), 7.40-7.53 (m, 6 H), 7.60-7.62 (m, 4 H), 7.90 (s, 2 H).

Aufarbeitung

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate concentrated
  3. dissolutionThe crude product was dissolved in EtOAc
  4. washwashed sequentially with sat. aq. NaHCO3 (3×), with 1 N HCl (3×), brine (3×)
  5. dry with materialdried (K2CO3)
  6. concentrationconcentrated
  7. customPurification on Biotage KP-Sil
  8. washeluting with 20% acetone/hexane

Quellen und Nachweise

ORD-Eintrag
ord-d6fb872090e848ddab656c03adad35a7
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06103708

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