Pyridine → 6-Phenoxypyrid-2-ylmethyl 1-(4-ethoxyphenyl)-2,2,3,3-tetrafluorocyclobutane carboxylate

HRID 231844Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 231844
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:18](Cl)=[O:19])[CH2:13][C:12]([F:15])([F:14])[C:11]2([F:17])[F:16])=[CH:6][CH:5]=1)[CH3:2].[OH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:24]=1.N1C=CC=CC=1>C1C=CC=CC=1.CCOCC>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:24]=3)=[O:19])[CH2:13][C:12]([F:15])([F:14])[C:11]2([F:16])[F:17])=[CH:6][CH:5]=1)[CH3:2]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 128791556-Phenoxy-2-pyridinemethanolHCID 135589381-(4-Ethoxyphenyl)-2,2,3,3-tetrafluorocyclobutane-1-carbonyl chloride

Produkt 1

HCID 200321336-Phenoxypyrid-2-ylmethyl 1-(4-ethoxyphenyl)-2,2,3,3-tetrafluorocyclobutane carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-(4-ethoxyphenyl)-2,2,3,3-tetrafluorocyclobutane carbonyl chloride (0.76 gm, 1.54 mmole) in dry benzene (10 ml) was added a solution of 2-hydroxymethyl-6-phenoxypyridine (0.305 g) and pyridine (0.12 g) in dry benzene (15 ml). The mixture was stirred at room temperature for 16 hours then diluted with ether, washed twice with water, dried over Na2SO4 and concentrated in vacuo. Purification by high pressure liquid chromatography gave the ester as a colourless oil. IR (film) λmax 1741, 1606, 1591, 1575, 1500, 1490, 1450 cm-1. N.m.r. (250 MHz) δ (CDCl3) 1.42, t, 3H, J=7 Hz, CH3 ; 2.90-3.08, m, 1H, cyclobutyl H; 3.44-3.64, m, 1H, cyclobutyl H; 4.02, q, 2H, J=7 Hz, CH2CH3 ; 5.10, 5.16, ABq, 2H, J=14.5 Hz, CH2 -O; 6.71-7.64, m, 13H, aromatic H's. Mass spectrum, m/z 476 (M+ +1), 456 (M+ -19).

Aufarbeitung

  1. washwashed twice with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customPurification by high pressure liquid chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ace76d447b274dc58d478e5b7e2c3b92
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04849450

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