Water → HCID 23294175, compound

HRID 1955001Notes

Reaction equation

HRID 1955001 reaction equation
[CH:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([O:12][CH2:13][C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=3[N:21]3[CH2:25][CH2:24][O:23][C:22]3=[O:26])[C:6]2=[N:5][C:4]=1[CH3:27])=[O:2].[BH4-].[Na+].O>C(O)C>[OH:2][CH2:1][C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([O:12][CH2:13][C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=3[N:21]3[CH2:25][CH2:24][O:23][C:22]3=[O:26])[C:6]2=[N:5][C:4]=1[CH3:27]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 23294182HCID 23294182, compound

Product 1

HCID 23294175HCID 23294175, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
4 °C

Procedure

A solution of 3-[2-(3-formyl-2-methylimidazo[1,2-a]pyridin-8-yloxymethyl)-3-methylphenyl]oxazolidin-2-one (1.39 g, 3.8 mmol) and sodium borohydride (0.19 g, 4.75 mmol) in anhydrous ethanol (125 ml) is stirred at RT for 1.5 h. Water (100 ml) is then added, the ethanol is distilled off on a rotary evaporator and the aqueous residue is stirred at 4° C. for 30 min. The precipitate is filtered off, washed with cold water and dried in vacuo. The title compound (1.28 g, 91%) is obtained as a beige solid. M.p. 190-193° C.

Workup

  1. distillationthe ethanol is distilled off on a rotary evaporator
  2. filtrationThe precipitate is filtered off
  3. washwashed with cold water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-6845300ee468491e91793e5293faa0fa
Source dataset
uspto-grants-2000_09
Patent number
US06124313

Reaction notes

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