Selenium Dioxide → HCID 89375787, compound

HRID 1752256Notes

Reaction equation

HRID 1752256 reaction equation
[CH3:1][C:2]1[O:7][CH2:6][CH2:5][CH2:4][C:3]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[Se](=O)=[O:14]>C(O)(=O)C>[CH:1]([C:2]1[O:7][CH2:6][CH2:5][CH2:4][C:3]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:14]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 82467Ethyl 3,4-dihydro-6-methyl-2H-pyran-5-carboxylate

Product 1

HCID 89375787HCID 89375787, compoundYield 26.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl 6-methyl-3,4-dihydro-2H-pyran-5-carboxylate (6.0 g, 35.3 mmol) and selenium dioxide (4.3 g, 38.8 mmol) was stirred in acetic acid (141 mL) 5 hours at 110° C. The reaction was then cooled to room temperature and the solids were removed by filtration. The filtrate was concentrated down and purified by silica gel chromatography with 0 to 15% ethyl acetate/heptane gradient, followed by 15% to afford the title compound (1.710 g) as an amber oil in about 90% purity. MS (ESI) [m/e, (M+H)+]=185.3. 1H NMR (400 MHz, chloroform-d) δ ppm 10.22 (s, 1H), 4.28 (q, J=7.24 Hz, 2H), 4.12-4.19 (m, 2H), 2.54 (t, J=6.57 Hz, 2H), 1.88-1.98 (m, 2H), 1.30-1.38 (m, 3H).

Workup

  1. customthe solids were removed by filtration
  2. concentrationThe filtrate was concentrated down
  3. custompurified by silica gel chromatography with 0 to 15% ethyl acetate/heptane gradient

Sources & evidence

ORD record
ord-cf540e55f9fb43948c711ecbc606947e
Source dataset
uspto-grants-2015_10
Patent number
US09163003B2

Reaction notes

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