Acetone → 4-(2-Carboxytridecyl)-5-hydroxy-2(5H)-furanone

HRID 345887

Reaktionsgleichung

Reaktionsgleichung von HRID 345887
[C:1]([CH:4]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:5][C:6]1C=C([Si](C)(C)C)[O:9][CH:10]=1)([OH:3])=[O:2].C1C(I)=C([OH:33])C(I)=C2OC3C(C4(OC(=O)C5C(Cl)=C(Cl)C(Cl)=C(Cl)C4=5)C=12)=CC(I)=C(O)C=3I.O=O.C[C:62]([CH3:64])=[O:63]>>[C:1]([CH:4]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:5][C:6]1[CH:10]([OH:9])[O:33][C:62](=[O:63])[CH:64]=1)([OH:3])=[O:2]

Komponenten

5

Edukt 4

HCID 180AcetoneHCID 977OxygenHCID 69439Rose Bengal LactoneHCID 199915924-(2-Carboxytridecyl)-2-trimethylsilylfuran

Produkt 1

HCID 199916244-(2-Carboxytridecyl)-5-hydroxy-2(5H)-furanone

Versuchsvorschrift

A mixture of 4-(2-carboxytridecyl)-2-trimethylsilylfuran (46.3 mg, 0.126 mmol) and Rose Bengal (5 mg) in acetone (10 ml) was exposed to singlet oxygen at -78° for 2 hours. The residue, after solvent removal, was purified by preparative TLC (20×20 cm, 500μ silica plate; developed with 10% MeOH/CHCl3 containing a few drops of acetic acid). The title compound was obtained as a colorless solid.

Aufarbeitung

  1. customThe residue, after solvent removal
  2. customwas purified by preparative TLC (20×20 cm, 500μ silica plate; developed with 10% MeOH/CHCl3 containing a few drops of acetic acid)

Quellen und Nachweise

ORD-Eintrag
ord-17112aadb3844ce6a3230bdfd59387bf
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05059611

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