2-Hydroxymethyl-3-(5-carboethoxypentyloxy)-6-(trimethylacetoxymethyl)-4-pyrone → 2-Formyl-3-(5-carboethoxypentyloxy)-6-(trimethylacetoxymethyl)-4-pyrone

HRID 2163265Notes

Reaction equation

HRID 2163265 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]

Participants

4

Reactant 1

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

Product 1

HCID 233448512-Formyl-3-(5-carboethoxypentyloxy)-6-(trimethylacetoxymethyl)-4-pyroneYield 70%

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 = 7Hz).

Workup

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

Sources & evidence

ORD record
ord-ae78c0e53f1b436fa32b02e94727233f
Source dataset
uspto-grants-1979_01
Patent number
US04132847

Reaction notes

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