Acetic Acid → HCID 18937643, Verbindung

HRID 2293320Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2293320
C([Li])CCC.C(NC(C)C)(C)C.[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[C:14]#[CH:15].[CH3:20][O:21][CH2:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[C:26]([N+:32]([O-:34])=[O:33])[CH:25]=1.C(O)(=O)C>O1CCCC1.O>[OH:29][CH:28]([C:27]1[CH:30]=[CH:31][C:24]([O:23][CH2:22][O:21][CH3:20])=[CH:25][C:26]=1[N+:32]([O-:34])=[O:33])[C:15]#[C:14][C:13]([O:17][CH2:18][CH3:19])=[O:16]

Komponenten

8

Edukt 5

HCID 176Acetic AcidHCID 7912DiisopropylamineHCID 12182Ethyl propiolateHCID 18937665HCID 18937665, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 18937643HCID 18937643, VerbindungAusbeute 105,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

1.5N butyllithium (19.3 ml, 29.0 mmole) was added under the argon atmosphere to a solution of diisopropylamine (4.3 ml, 30.6 mmole) in tetrahydrofuran (50 ml) at -78° C., and the mixture was stirred for 1 hour. Next, ethyl propiolate (2.4 ml, 23.7 mmole) and a solution of 4-methoxymethoxy-2-nitrobenzaldehyde (3.6 g, 17.0 mmole) in tetrahydrofuran (35 ml) were added in this sequence, and the reaction mixture was stirred at -78° C. for further 2 hours. After a solution of acetic acid (5.0 ml, 87.5 mmole) in tetrahydrofuran (20 ml) and water were sequentially added, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid, water, a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous saline in this sequence. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure to give ethyl 4-hydroxy-4(4-methoxymethoxy-2-nitrophenyl)-2-butynoate as an oil (5.53 g).

Aufarbeitung

  1. stirringthe reaction mixture was stirred at -78° C. for further 2 hours
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with dilute hydrochloric acid, water
  4. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e6ac757c8f5947a1921d7e2e218cd0b2
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05686442

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