Benzyl 2-(2-pyridyloxy)-2-methylbutanoate → HCID 22270592, compound

HRID 1394549Notes

Reaction equation

HRID 1394549 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][C:8]([CH3:21])([CH2:19][CH3:20])[C:9]([O:11]CC1C=CC=CC=1)=[O:10]>[Pd].CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][C:8]([CH3:21])([CH2:19][CH3:20])[C:9]([OH:11])=[O:10]

Participants

4

Reactant 1

HCID 22270398Benzyl 2-(2-pyridyloxy)-2-methylbutanoate

Product 1

HCID 22270592HCID 22270592, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 2-(2-pyridyloxy)-2-methylbutanoate (1.6 g, 5.5 mmol) and 10% palladium on carbon (50 mg) in 50 mL of methanol was degassed and filled with hydrogen using a balloon. After stirring at room temperature overnight, the reaction mixture was filtered through CELITE diatomaceous earth and washed with methanol (20 mL), and the filtrate was concentrated to dryness to give the title compound. 1H NMR (500 MHz, CD3OD): δ 8.03 (dd, 1H), 7.64 (ddd, 1H), 6.89 (dd, 1H), 6.76 (dd, 1H), 2.14 (m, 1H), 1.94 (m, 1H), 1.64 (s, 3H), 0.99 (t, 3H). LC-MS: m/e 196 (M+H)+ (1.8 min).

Workup

  1. customwas degassed
  2. additionfilled with hydrogen using a balloon
  3. filtrationthe reaction mixture was filtered through CELITE diatomaceous earth
  4. washwashed with methanol (20 mL)
  5. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-a5d56ce619664e88bebf417c16b447fc
Source dataset
uspto-grants-2008_03
Patent number
US07348456B2

Reaction notes

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