Sodium Hydroxide → HCID 69318434, compound

HRID 1393341Notes

Reaction equation

HRID 1393341 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[O:12][CH:13]=[C:14]([CH2:16][C:17](O)=[O:18])[N:15]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[O:12][CH:13]=[C:14]([CH2:16][CH2:17][OH:18])[N:15]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 69317496HCID 69317496, compound

Product 1

HCID 69318434HCID 69318434, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl ester of [2-(2-naphthyl)-oxazol-4-yl]acetic acid (434 mg, 1.54 mmol) in tetrahydrofuran (20 ml) was added dropwise to a suspension of lithium aluminium hydride (66 mg, 1.74 mmol) in tetrahydrofuran (15 ml) with stirring under ice cooling and the mixture was stirred at the same temperature for 2.5 hrs. To the reaction mixture were added water (0.1 ml), 15% aqueous solution of sodium hydroxide (0.1 ml), water (0.3 ml) and sodium sulfate (3 g )in turn. Insoluble materials were filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=2−1) to give 2-[2-(2-naphthyl)-oxazol-4-yl]ethanol (323 mg, 88%) as pale yellow crystals.

Workup

  1. stirringthe mixture was stirred at the same temperature for 2.5 hrs
  2. filtrationInsoluble materials were filtered off
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=2−1)

Sources & evidence

ORD record
ord-4c783aae1749481da590f0741743610a
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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