Tetrahydrofuran → HCID 86672213, compound

HRID 79361Notes

Reaction equation

HRID 79361 reaction equation
[CH3:1][O:2][C:3]1[N:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:4]=1[C:5]([O:7]C)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].[CH2:37]1COC[CH2:38]1>>[CH2:37]([CH:5]([C:4]1[C:3]([O:2][CH3:1])=[N:12][C:11]([CH3:13])=[CH:10][CH:9]=1)[OH:7])[CH3:38]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 62649Sodium sulfate decahydrateHCID 10910170METHYL 2-METHOXY-6-METHYLPYRIDINE-3-CARBOXYLATEHCID 21226445Aluminium lithium hydride

Product 1

HCID 86672213HCID 86672213, compound

Conditions

Temperature
0 °C

Procedure

To methyl 2-methoxy-6-methylnicotinate (5.60 g, 30.9 mmol) in THF (155 mL, 30.9 mmol) to 0° C. was added lithium aluminum hydride (1.23 g, 30.9 mmol) and the mixture was stirred at 0° C. for 75 minutes. The mixture was diluted with 30 mL THF and a scoop of Celite was added. The mixture was stirred for a few minutes. Sodium sulfate decahydrate was added to quench the reaction. The mixture was filtered and the filtrate was concentrated to give the product (4.7 g).

Workup

  1. additiona scoop of Celite was added
  2. stirringThe mixture was stirred for a few minutes
  3. customto quench
  4. customthe reaction
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a20c86094b5b4575acd71a23ee8ea2fb
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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