Propanal → 2-(2-Oxobutyl)-4-hydroxy-1-indanone

HRID 974781Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 974781
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[CH:12](=[O:15])[CH2:13][CH3:14].C(N([CH2:21][CH3:22])CC)C.[CH2:23]([OH:25])[CH3:24]>[I-].C[N+]1C(C)=C(CCO)SC=1.C(Cl)Cl>[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[CH2:12])[C:8]2=[O:11])=[CH:4][CH:3]=1.[O:15]=[C:12]([CH2:21][CH3:22])[CH2:13][CH:14]1[CH2:2][C:10]2[C:9](=[CH:5][CH:4]=[CH:24][C:23]=2[OH:25])[C:8]1=[O:11]

Komponenten

8

Edukt 4

HCID 527PropanalHCID 702EthanolHCID 8471TriethylamineHCID 70206596-Hydroxy-1-indanone

Produkt 2

HCID 199694252-(2-Oxobutyl)-4-hydroxy-1-indanoneAusbeute 70 %HCID 199694276-Hydroxy-2-methylene-1-indanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 98387703,4-Dimethyl-5-(2-hydroxyethyl)thiazolium iodideKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

6-Hydroxy-2-methylene-1-indanone was prepared using a similar method to that described in Example 16 but using 6-hydroxy-1-indanone instead of 4-hydroxy-1-indanone. To the above compound (0.3 g; 1.87 mmol) in suspension in ethanol, were added, at ambient temperature, under argon: propionaldehyde (0.27 ml; 3.75 mmol), triethylamine (80 μl; 0.56 mmol) and 3,4-dimethyl-5-(2hydroxyethyl)thiazolium iodide (50.6 mg; 0.18 mmol). The mixture was heated at 80° C. for 17 hours. The solution was taken up in CH2Cl2 and washed in water and a saturated solution of NaCl. The organic phase was dried over MgSO4, filtered and evaporated. The residue was purified by flash chromatography on silica gel, eluting with petroleum ether/ethyl acetate (7/3), to give 2-(2-oxobutyl)-4-hydroxy-1-indanone (0.28 g; 70%).

Aufarbeitung

  1. washwashed in water
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel
  6. washeluting with petroleum ether/ethyl acetate (7/3)

Quellen und Nachweise

ORD-Eintrag
ord-7cb3c88aa8c04ff1a59864567197c248
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05607928

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