Tetrahydrofuran → HCID 58306590, compound

HRID 1909862Notes

Reaction equation

HRID 1909862 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([O:12][CH3:13])=[O:11])=[N:8][CH:9]=1)(=[O:3])[CH3:2].C1COCC1.[BH4-].[Na+]>CO>[OH:3][CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([O:12][CH3:13])=[O:11])=[N:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 54000692HCID 54000692, compound

Product 1

HCID 58306590HCID 58306590, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of methyl 5-acetylpyridine-2-carboxylate (1.00 g), THF (24 mL), and methanol (12 mL) was added sodium borohydride (110 mg), followed by stirring at room temperature for 2 hours. The mixture was concentrated under reduced pressure, and then to the obtained residue was added a saturated aqueous sodium chloride solution. After extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated and then dried under reduced pressure to obtain methyl 5-(1-hydroxyethyl)pyridine-2-carboxylate (897 mg).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionto the obtained residue was added a saturated aqueous sodium chloride solution
  3. extractionAfter extraction with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-12bb96898a94486486939993fa49829e
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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