2-Benzyloxy-3-pyridinecarbaldehyde → 4-[3-(2-Benzyloxy-3-pyridyl)prop-2-enyl]benzoic acid

HRID 2395073Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2395073
[Br-].[C:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:7][CH:6]=1)([OH:4])=[O:3].[CH2:32]([O:39][C:40]1[C:45]([CH:46]=O)=[CH:44][CH:43]=[CH:42][N:41]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1COCC1>[CH2:32]([O:39][C:40]1[C:45]([CH:46]=[CH:12][CH2:11][C:8]2[CH:7]=[CH:6][C:5]([C:2]([OH:4])=[O:3])=[CH:10][CH:9]=2)=[CH:44][CH:43]=[CH:42][N:41]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Komponenten

4

Edukt 2

HCID 189739592-Benzyloxy-3-pyridinecarbaldehydeHCID 226755274-Carboxyphenethyltriphenylphosphonium bromide

Produkt 1

HCID 538770954-[3-(2-Benzyloxy-3-pyridyl)prop-2-enyl]benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

(2-(4-Carboxyphenyl)ethyl)triphenylphosphonium bromide (10.9 g, 22.2 mmol) was suspended in THF (80 ml) and the flask was flushed with argon. Lithium bis(trimethylsilyl)amide (1M in THF, 48.8 ml) was added dropwise and the reaction stirred for 1 hour, becoming dark brown. A solution of 2-benzyloxy-3-pyridinecarbaldehyde (4.73 g, 22.2 mmol) in THF (20 ml) was added slowly. The reaction was stirred at ambient temperature for 18 hours (shielding from light alumimium foil). The reaction mixture was then partitioned between Et2O/water, the organic layer was washed with water and the aqueous layers were combined, acidified with HCl and extracted with EtOAc. The organic phase was dried (MgSO4) and evaporated and purified by colum chromtagraphy with MeOH/CH2Cl2 to give the title product.

Aufarbeitung

  1. customthe flask was flushed with argon
  2. additionLithium bis(trimethylsilyl)amide (1M in THF, 48.8 ml) was added dropwise
  3. stirringThe reaction was stirred at ambient temperature for 18 hours (shielding from light alumimium foil)
  4. customThe reaction mixture was then partitioned between Et2O/water
  5. washthe organic layer was washed with water
  6. extractionextracted with EtOAc
  7. dry with materialThe organic phase was dried (MgSO4)
  8. customevaporated
  9. custompurified by colum chromtagraphy with MeOH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-1959a29c08ff49b081fea1b788f276ff
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05811459

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