Tetrahydrofuran → N-(4-decylphenyl)-2-hydroxy-[1,1'-biphenyl]-3-carboxamide

HRID 2165096

Reaktionsgleichung

Reaktionsgleichung von HRID 2165096
O1CCCC1.[CH2:6]([C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C([Li])CCC.[C:28]1([C:34]2[CH:43]=[CH:42][CH:41]=[C:36]([C:37](OC)=[O:38])[C:35]=2[OH:44])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>ClCCl>[CH2:6]([C:16]1[CH:17]=[CH:18][C:19]([NH:20][C:37]([C:36]2[C:35]([OH:44])=[C:34]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:43]=[CH:42][CH:41]=2)=[O:38])=[CH:21][CH:22]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Komponenten

6

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 923094-DecylanilineHCID 241577Methyl 2-hydroxy-3-phenylbenzoateHCID 178418339Butyllithium

Produkt 1

HCID 23043616N-(4-decylphenyl)-2-hydroxy-[1,1'-biphenyl]-3-carboxamideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a tetrahydrofuran (20 ml) solution of 4-decylaniline (3.07 g, 13.14 mmol), cooled to 0°-5° C. (inert atmosphere), is added n-butyllithium (2.3 M, 13.14 mmol). The deeply colored solution is stirred for ten minutes, after which a tetrahydrofuran (20 ml) solution of methyl 3-phenylsalicylate (1.00 g, 4.38 mmol) is added. The temperature is allowed to rise to 25° C. over a 30 minute period. The reaction is quenched by pouring the contents into 10% hydrochloric acid (100 ml). The organics are extracted into ethyl acetate, washed with 10% hydrochloric acid, dried (sodium sulfate), and concentrated to give 2.77 g of crude solid. Chromatography (Kieselgel 60, dichloromethane) affords N-(4-decylphenyl)-2-hydroxy-[1,1'-biphenyl]-3-carboxamide (1.69 g, 90%), mp 74°-75° C.

Aufarbeitung

  1. customThe reaction is quenched
  2. additionby pouring the contents into 10% hydrochloric acid (100 ml)
  3. extractionThe organics are extracted into ethyl acetate
  4. washwashed with 10% hydrochloric acid
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated
  7. customto give 2.77 g of crude solid

Quellen und Nachweise

ORD-Eintrag
ord-1edfb796a5e84ba8bb90232aa25fb128
Quelldatensatz
uspto-grants-1990_07
Patentnummer
US04939133

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