Sodium borohydride → HCID 21276372, compound

HRID 247378Notes

Reaction equation

HRID 247378 reaction equation
[CH:1]([C:3]1[C:16]2[O:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([CH:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH3:18])[C:7]=2[CH:6]=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+]>C(O)C>[OH:2][CH2:1][C:3]1[C:16]2[O:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([CH:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH3:18])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 14031260HCID 14031260, compound

Product 1

HCID 21276372HCID 21276372, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 3.9 g (12.3 mmoles) of 4-formyl-N-(α-phenylethyl)phenoxazine, 250 ml of ethanol and 0.594 g (18.5 mmoles) of sodium borohydride was heated at 40° C. under stirring during 15 minutes. The solvent was then removed under reduced pressure and the residue diluted with water and extracted with ethyl acetate (2×100 ml). The combined extracts were dried and the solvent removed under reduced pressure. The oily residue (3.5 g) was percolated through a short column of silica gel using ether as the solvent, to yield 4-hydroxymethyl-N-(α-phenylethyl)phenoxazine, as an oil

Workup

  1. customThe solvent was then removed under reduced pressure
  2. additionthe residue diluted with water
  3. extractionextracted with ethyl acetate (2×100 ml)
  4. customThe combined extracts were dried
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-d98aa8fbc22542888cc106808c0a03d3
Source dataset
uspto-grants-1987_11
Patent number
US04707473

Reaction notes

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