Toluene → 4-[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enal

HRID 32967

Reaktionsgleichung

Reaktionsgleichung von HRID 32967
[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:4]=1[CH2:21]C=O.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[C:31]([CH3:34])[CH:32]=[O:33])C=CC=CC=1.[C:47]1(C)C=CC=CC=1>>[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([O:14][CH2:15][CH2:16][Si:17]([CH3:18])([CH3:20])[CH3:19])[C:4]=1[CH2:21][CH:47]=[C:31]([CH3:34])[CH:32]=[O:33]

Komponenten

4

Edukt 3

HCID 1140TolueneHCID 42809872-(Triphenylphosphoranylidene)propionaldehyde2×HCID 57478686[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-acetaldehyde

Produkt 1

HCID 765461944-[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enalAusbeute 83 %

Versuchsvorschrift

[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-acetaldehyde (70 mg, 0.21 mmol) in toluene (2 mL) was heated at 100° C. with 2-(triphenyl-phosphanylidene)-propionaldehyde (72.9 mg, 0.23 mmol) overnight. A second portion of 2-(triphenyl-phosphanylidene)-propionaldehyde (33 mg, 0.11 mmol) was added and the reaction mixture was heated for an additional day. After concentration, the residue was purified by silica gel chromatography to provide 54 mg (83%) of the desired product as a pale yellow oil. 1H NM (300 MHz, CDCl3) δ 0.00 (s, 9H), 1.10-1.21 (m, 2H), 1.87 (s, 3H), 2.16 (s, 3H), 3.67-3.76 (m, 2H), 3.74 (s, 3H), 4.27-4.39 (m, 2H), 5.11 (s, 2H), 6.40-6.48 (m, 1H), 9.2 (s, 1H) ppm.

Aufarbeitung

  1. temperaturethe reaction mixture was heated for an additional day
  2. concentrationAfter concentration
  3. customthe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-28a702cfb54a489ba78324415e82c391
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427636B2

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