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Dimethylformamide → 5-(2,6-Dimethyl-4-triisopropylsilanyloxybenzyl)-2-methoxymethoxybenzaldehyde

HRID 1170994
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1170994
[CH3:1][C:2]1[CH:18]=[C:17]([O:19][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])[CH:16]=[C:15]([CH3:30])[C:3]=1[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][O:13][CH3:14])=[CH:7][CH:6]=1.CN(CCN(C)C)C.[Li]CCCC.CN([CH:47]=[O:48])C>CCOCC>[CH3:30][C:15]1[CH:16]=[C:17]([O:19][Si:20]([CH:27]([CH3:29])[CH3:28])([CH:21]([CH3:23])[CH3:22])[CH:24]([CH3:26])[CH3:25])[CH:18]=[C:2]([CH3:1])[C:3]=1[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][O:13][CH3:14])=[C:7]([CH:6]=1)[CH:47]=[O:48]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 666426914-(2,6-Dimethyl-4-triisopropylsilanyloxybenzyl)-methoxymethoxybenzeneHCID 178418339Butyllithium

Produkt 1

HCID 866034575-(2,6-Dimethyl-4-triisopropylsilanyloxybenzyl)-2-methoxymethoxybenzaldehydeAusbeute 98,7 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 4-(2,6-dimethyl-4-triisopropylsilanyloxybenzyl)-methoxymethoxybenzene (2.0 g, 4.66 mmol) in ether was added TMEDA (1.05 mL, 6.99 mmol), followed by nBuLi (2.5 M in THF, 2.8 mL) at −20° C. The reaction mixture was warmed up to 0° C. and stirred for 1 h DMF (0.72 mL, 9.32 mmol) was then added and after stirring at 0° C. for 2 h, the reaction mixture was quenched with a saturated solution of NH4Cl and diluted with EtOAc. The water layer was extracted with EtOAc and the combined organic extracts were dried (MgSO4), filtered and concentrated to give the crude product 5-(2,6-dimethyl-4-triisopropylsilanyloxybenzyl)-2-methoxymethoxy-benzaldehyde (2.1 g, 98%): 1H NMR (300 MHz, d6-DMSO): δ 10.33 (s, 1H), 7.24 (m, 3H), 6.58 (s, 2H), 5.31 (s, 2H), 3.91 (s, 2H), 3.33 (s, 6H), 1.23 (m, 3H), 1.06 (m, 18H). TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate-hexanes (1:9); Rf=0.55.

Aufarbeitung

  1. additionwas then added
  2. customthe reaction mixture was quenched with a saturated solution of NH4Cl
  3. additiondiluted with EtOAc
  4. extractionThe water layer was extracted with EtOAc
  5. dry with materialthe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a0672c0d47e1436492d4c4e01169bc1f
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07829552B2

Notizen zur Reaktion

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