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5-Diethylphosphono-2-thiophenecarboxaldehyde → 3-{[5-(Diethoxy-phosphoryl)-thiophen-2-yl]-hydroxy-methyl}-5-isopropoxy-benzoic acid

HRID 1431006
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1431006
Br[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH:12]([CH3:14])[CH3:13])[CH:10]=1)[C:5]([OH:7])=[O:6].[Li]CCCC.[CH2:20]([O:22][P:23]([C:28]1[S:29][C:30]([CH:33]=[O:34])=[CH:31][CH:32]=1)(=[O:27])[O:24][CH2:25][CH3:26])[CH3:21]>C1COCC1>[CH2:20]([O:22][P:23]([C:28]1[S:29][C:30]([CH:33]([OH:34])[C:2]2[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH:12]([CH3:14])[CH3:13])[CH:10]=2)[C:5]([OH:7])=[O:6])=[CH:31][CH:32]=1)([O:24][CH2:25][CH3:26])=[O:27])[CH3:21]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 222749525-Diethylphosphono-2-thiophenecarboxaldehydeHCID 532166663-Bromo-5-isopropoxybenzoic acidHCID 178418339Butyllithium

Produkt 1

HCID 866595583-{[5-(Diethoxy-phosphoryl)-thiophen-2-yl]-hydroxy-methyl}-5-isopropoxy-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 3-bromo-5-isopropoxy-benzoic acid (2.0 g, 8.26 mmol) in THF (30 ml) was added 1.6 M nBuLi (10.6 ml, 16.94 mmol) at −78° C. The reaction was stirred at −78° C. for 1 h and treated with a solution of (5-formyl-thiophen-2-yl)-phosphonic acid diethyl ester (2.5 g, 9.91 mmol) in THF. After stirring at −78° C. for 30 min, the reaction mixture was warmed up to r.t. and quenched by water, diluted with EtOAc. The aqueous layer was separated, acidified with 2N HCl to pH<1, and extracted with EtOAc (3×). The combined EtOAc layers were dried over MgSO4, filtrated, concentrated to give the crude product 3-{[5-(diethoxy-phosphoryl)-thiophen-2-yl]-hydroxy-methyl}-5-isopropoxy-benzoic acid.

Aufarbeitung

  1. stirringAfter stirring at −78° C. for 30 min
  2. temperaturethe reaction mixture was warmed up to r.t.
  3. customquenched by water
  4. additiondiluted with EtOAc
  5. customThe aqueous layer was separated
  6. extractionextracted with EtOAc (3×)
  7. dry with materialThe combined EtOAc layers were dried over MgSO4
  8. filtrationfiltrated
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-180298702bf340e8bdb7da94082b2188
Quelldatensatz
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08940927B2

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