Methanol → HCID 58307466, compound

HRID 222791

Reaction equation

HRID 222791 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:14])=[CH:8][C:9](=O)[O:10][C:11]=1[CH3:12])=[O:5])[CH3:2].Cl.[NH2:16][NH2:17].CO>C([O-])([O-])=O.[K+].[K+]>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:14])=[CH:8][C:9](=[O:10])[N:16]([NH2:17])[C:11]=1[CH3:12])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 76918ethyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylateHCID 115031Hydrazinium chloride

Product 1

HCID 58307466HCID 58307466, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylic acid ethyl ester (3.2 mL, 19 mmol) and hydrazine monohydrochloride (1.4 g, 20 mmol) in methanol (16 mL, 0.39 mmol) was heated under microwave irradiation for 2.5 hrs at 150° C. Reaction was taken up in sat. aq. K2CO3 (40 mL) and extracted with ethyl acetate (3×40 mL). The combined organic phases were washed with brine, dried over MgSO4, evaporated and purified by flash chromatography. Yield 7%. 1H NMR (500 MHz, CDCl3): 6.35 (s, 1H), 5.12 (s, 2H), 4.35 (q, J=7.1 Hz, 2H), 2.53 (s, 3H), 2.21 (s, 3H), 1.37 (t, J=7.1 Hz, 3H).

Workup

  1. customReaction
  2. extractionextracted with ethyl acetate (3×40 mL)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-cafca3c763bb4a119ded67a4451b45ac
Source dataset
uspto-grants-2012_06
Patent number
US08207347B2

Linked notes

Loading…