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2-Iodoxybenzoic acid → 3-Isobutyryl-1,8-dioxaspiro[4.5]dec-3-en-2-one

HRID 1747707
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1747707
O.COC1C=C[N+]([O-])=CC=1.I(C1C=CC=CC=1C(O)=O)(=O)=O.[C:23]([CH:28]1[CH2:32][C:31]2([CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[O:30][C:29]1=[O:38])(=[O:27])[CH:24]([CH3:26])[CH3:25]>CS(C)=O.C(=O)(O)[O-].[Na+].O>[C:23]([C:28]1[C:29](=[O:38])[O:30][C:31]2([CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[CH:32]=1)(=[O:27])[CH:24]([CH3:26])[CH3:25]
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Komponenten

7

Edukt 3

HCID 1087942-Iodoxybenzoic acidHCID 162122934-Methoxypyridine N-oxide hydrateHCID 667618043-Isobutyryl-1,8-dioxaspiro[4.5]decan-2-one

Produkt 1

HCID 667628553-Isobutyryl-1,8-dioxaspiro[4.5]dec-3-en-2-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittel
HCID 962
Water
Lösungsmittel
HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

2.16 g 4-Methoxypyridine-1-oxide hydrate and 5.57 g 2-iodoxybenzoic acid (45 wt-%) are suspended in 20 ml dimethylsulfoxide and stirred for 20 minutes until all material has dissolved. Then 3.0 g 3-isobutyryl-1,8-dioxaspiro[4.5]decan-2-one are added and the mixture is stirred for 24 hours. The mixture is diluted with saturated solution of sodium bicarbonate in water and the formed precipitate is filtered off. The mother liquour is extracted for three times with ethylacetate. The combined organic phases are dried with sodium sulphate and the solvents are evaporated in vacuo. The residue is chromatographed on silica gel (petrole ether/ethylacetate 100:0 to 40:60).

Aufarbeitung

  1. dissolutionhas dissolved
  2. stirringthe mixture is stirred for 24 hours
  3. filtrationthe formed precipitate is filtered off
  4. extractionThe mother liquour is extracted for three times with ethylacetate
  5. dry with materialThe combined organic phases are dried with sodium sulphate
  6. customthe solvents are evaporated in vacuo
  7. customThe residue is chromatographed on silica gel (petrole ether/ethylacetate 100:0 to 40:60)

Quellen und Nachweise

ORD-Eintrag
ord-d54c5efb120a4c7ab73994e77517dacf
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09150583B2

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