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

HRID 573783Notes

Reaction equation

HRID 573783 reaction equation
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]

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

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 liquor 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).

Workup

  1. dissolutionhas dissolved
  2. stirringthe mixture is stirred for 24 hours
  3. filtrationthe formed precipitate is filtered off
  4. extractionThe mother liquor 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)

Sources & evidence

ORD record
ord-6d51a94190364c88ba34cb9122f8c9ae
Source dataset
uspto-grants-2015_05
Patent number
US09029544B2

Reaction notes

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