2-Hydroxymethyl-3-(5-carboethoxypentyloxy)-6-(trimethylacetoxymethyl)-4-pyrone → 4H-pyran-4-one

HRID 1856398Notes

Reaction equation

HRID 1856398 reaction equation
[OH:1][CH2:2][C:3]1[O:4][C:5]([CH2:21][O:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:6][C:7](=[O:20])[C:8]=1[O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>CC(C)=O.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[O:4][C:5]([CH2:21][O:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:6][C:7](=[O:20])[C:8]=1[O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:1].[O:4]1[CH:5]=[CH:6][C:7](=[O:20])[CH:8]=[CH:3]1

Participants

5

Reactant 1

HCID 233448562-Hydroxymethyl-3-(5-carboethoxypentyloxy)-6-(trimethylacetoxymethyl)-4-pyrone

Product 2

HCID 79684H-pyran-4-oneYield 577%HCID 233448512-Formyl-3-(5-carboethoxypentyloxy)-6-(trimethylacetoxymethyl)-4-pyrone

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent

Procedure

To a solution of 2.3 g of 2-hydroxymethyl-3-(5-carboethoxypentyloxy)-6-(trimethylacetoxymethyl)-4-pyrone in 75 ml of acetone was added 4 g of activated manganese dioxide. The resulting suspension was stirred for 3 hr, at which time the mixture was filtered and the filtrate evaporated to an oil. The oil was chromatographed on silica gel to give the oily aldehyde, 2-formyl-3-(5-carboethoxypentyloxy)-6-trimethylacetoxymethyl)-4-pyrone weighing 1.6 g (70%). NMR (CDCl3): δ1.28 (3H, t, J=7 Hz), 1.30 (9H, s), 2.31 (2H, t, J=5.5 Hz), 4.17 (2H, q, J=7 Hz), 4.48 (2H, t, J=7 Hz).

Workup

  1. filtrationwas filtered
  2. customthe filtrate evaporated to an oil
  3. customThe oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-04b802dc333e445898cefaed9bcffeab
Source dataset
uspto-grants-1980_08
Patent number
US04219483

Reaction notes

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