Methanol → HCID 11391236, Verbindung

HRID 1685326Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1685326
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[N+:11]([O-:13])=[O:12])=[CH:5][CH:4]=1.[Li][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1.CO.[NH4+].[Cl-]>C1COCC1.[Cl-].[Na+].O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:10][N+:11]([O-:13])=[O:12])=[CH:7][CH:8]=1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 697963trans-4-Methoxy-beta-nitrostyreneHCID 178506676HCID 178506676, Verbindung

Produkt 1

HCID 11391236HCID 11391236, VerbindungAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a cold (−78° C.), stirred solution of (E)-1-methoxy-4-(2-nitrovinyl)benzene (153 mg, 0.86 mmol) in THF (20 mL) was added PhLi (0.64 mL, 1.6M) under Ar. After 1.5 h, the reaction was treated with MeOH, sat. NH4Cl and brine, and allowed to warm to room temperature. The reaction was extracted with EtOAc (3×), dried (MgSO4), filtered, concentrated then purified on Biotage Horizon to provide the product (150 mg, 68%) as an oil: 1H NMR (400 MHz, CDCl3) δ ppm: 7.32 (2H, t, J=7.20 Hz), 7.19-7.25 (3H, m), 7.14 (2H, d, J=8.84 Hz), 6.84 (2H, d, J=8.84 Hz), 4.90-4.96 (2H, m), 4.81-4.87 (1H, m), 3.77 (3H, s).

Aufarbeitung

  1. extractionThe reaction was extracted with EtOAc (3×)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthen purified on Biotage Horizon

Quellen und Nachweise

ORD-Eintrag
ord-5c3a25fb906b48208da953184c5cbc35
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148400B2

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