Diethyl 3,6-dihydro-2H-pyran-2,2-dicarboxylate → 73690-99-0

HRID 520428Notes

Reaction equation

HRID 520428 reaction equation
[O:1]1[CH2:6][CH:5]=[CH:4][CH2:3][C:2]1([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8]>CCOC(C)=O.[Pd]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C:2]1([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 1

HCID 556968Diethyl 3,6-dihydro-2H-pyran-2,2-dicarboxylate

Product 1

HCID 1252434273690-99-0

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A stirred suspension of 10% Pd—C (0.511 g, 0.480 mmol) in a solution of diethyl 2H-pyran-2,2(3H,6H)-dicarboxylate (2.74 g, 12.00 mmol) in EtOAc (50 mL) was hydrogenated under balloon pressure for 3 h. The suspension was filtered and the filtrate was evaporated to dryness to afford diethyl tetrahydro-2H-pyran-2,2-dicarboxylate as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.33-4.24 (m, 4H), 3.88-3.81 (m, 2H), 2.15-2.08 (m, 2H), 1.79-1.69 (m, 2H), 1.67-1.57 (m, 2H), 1.33-1.28 (m, 6H).

Workup

  1. filtrationThe suspension was filtered
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-3e7f7c532b544c699a0d9ad9c2219335
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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