Water → HCID 53844281, compound

HRID 636701Notes

Reaction equation

HRID 636701 reaction equation
[C:1]1([C:7]2[O:8][CH:9]=[C:10]([CH2:12][CH2:13][O:14][C:15]3[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=3)[CH:18]=[O:19])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].O>CC(O)C>[C:1]1([C:7]2[O:8][CH:9]=[C:10]([CH2:12][CH2:13][O:14][C:15]3[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=3)[CH2:18][OH:19])[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 18617256HCID 18617256, compound

Product 1

HCID 53844281HCID 53844281, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

14.0 g (47.9 mM) of 3-[2-(2-phenyl-4-oxazolyl)ethoxy]benzaldehyde, prepared as described in Preparation 2 herein, was diluted with 200 mL i-PrOH and treated with 2.89 g (76.6 mM) of sodium borohydride. The mixture was stirred at ambient temperature for 24 hr. 250 mL of H2O was added slowly over a period of 1 hr to quench the reaction and the resulting mixture was stirred for 1 hr. It was then concentrated under reduced pressure and the residue was diluted with 300 mL EtOAc and washed with H2O (300 mL) and brine (300 mL). All the organics were combined, dried over MgSO4, and concentrated to yield 13.6 g of a yellow waxy solid.

Workup

  1. customas described in Preparation 2 herein
  2. customto quench
  3. customthe reaction
  4. stirringthe resulting mixture was stirred for 1 hr
  5. concentrationIt was then concentrated under reduced pressure
  6. additionthe residue was diluted with 300 mL EtOAc
  7. washwashed with H2O (300 mL) and brine (300 mL)
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customto yield 13.6 g of a yellow waxy solid

Sources & evidence

ORD record
ord-5f288b52aa7742c9b9d1fab0a6d3ff49
Source dataset
uspto-grants-2001_02
Patent number
US06194446B1

Reaction notes

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