Sodium borohydride → HCID 11062593, compound

HRID 1638234Notes

Reaction equation

HRID 1638234 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[C:6]([CH3:9])=[CH:5][O:4][C:3]=1[C:10](OC)=[O:11].[BH4-].[Na+]>CO>[CH3:1][C:2]1[C:7](=[O:8])[C:6]([CH3:9])=[CH:5][O:4][C:3]=1[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11126890HCID 11126890, compound

Product 1

HCID 11062593HCID 11062593, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3,5-Dimethyl-2-methoxycarbonyl-4-pyrone 3 (R=Methyl) (294 mg, 1.62 mmol) and sodium borohydride (154 mg, 4.07 mmol) were dissolved in methanol (10 ml) and the resulting solution stirred at room temperature for 45 minutes. Silica gel (5 ml) was added and the solvent evaporated. The residue was applied to a pre-packed chromatography column assembled from silica gel (45 ml) in dichloromethane: ethyl acetate (1:1, v/v). Elution with firstly dichloromethane: ethyl acetate (1:1, v/v), then ethyl acetate, then methanol: ethyl acetate (1:3, v/v) gave 3,5-dimethyl-2-hydroxymethyl-4-pyrone 4 (230 mg, 92%) as a white solid. 1H-NMR (CDCl3) δ 1.93 (s, 3H), 2.01 (s, 3H), 4.60 (s, 2H), 7.71 (s, 1H); selected IR (cm-1, nujol) 3150-3500 (br, s), 1653 (s); Ms (APCI+) m/z (%) 155 (MH+, 100).

Workup

  1. additionSilica gel (5 ml) was added
  2. customthe solvent evaporated
  3. washElution with firstly dichloromethane: ethyl acetate (1:1

Sources & evidence

ORD record
ord-3f0b49e173394cf599166e8b6061b15e
Source dataset
uspto-grants-2000_03
Patent number
US06043371

Reaction notes

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