Acetic Acid → HCID 6496944, compound

HRID 2288940Notes

Reaction equation

HRID 2288940 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1)[C:2]1C=CC=CC=1.[CH3:16][NH2:17].[C:18](O)(=O)[CH3:19].C(O[BH-](O[C:32](=O)[CH3:33])OC(=O)C)(=O)C.[Na+].[CH2:36](O)C>Cl>[C:8]1([O:1][CH2:2][CH2:16][NH2:17])[CH:9]=[CH:10][C:11]([C:12]2[CH:19]=[CH:18][CH:33]=[CH:32][CH:36]=2)=[CH:14][CH:15]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 702EthanolHCID 6329MethylamineHCID 661394-PhenoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 6496944HCID 6496944, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 4-phenoxybenzaldehyde (4.4 ml, 25 mmol) in ethanol (50 ml) was added methylamine (3.0 ml of 33% solution in ethanol, 25 mmol) and acetic acid (1.4 ml, 25 mmol), and the mixture was stirred under an atmosphere of nitrogen. After 20 minutes sodium tri(acetoxy)borohydride (10.5 g, 50 mmol) was added and stirring was continued for 16 hours. The mixture was diluted with 2 M aqueous hydrochloric acid (200 ml) and washed with diethyl ether (2×100 ml). The aqueous layer was basified to pH 12 with concentrated aqueous ammonia solution and extracted with dichloromethane (4×100 ml). The combined organic layers were dried (Na2SO4), the solvent was evaporated under reduced pressure and the residue was purified by flash chromatography on silica gel (dichloromethane/methanol/aqueous ammonia solution 95:5:0 to 94:5:1) to give the titled compound as a colourless oil (3.3 g).

Workup

  1. stirringstirring
  2. washwashed with diethyl ether (2×100 ml)
  3. extractionextracted with dichloromethane (4×100 ml)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was purified by flash chromatography on silica gel (dichloromethane/methanol/aqueous ammonia solution 95:5:0 to 94:5:1)

Sources & evidence

ORD record
ord-47fe5c0196674a9288b305c30b880ffd
Source dataset
uspto-grants-2000_07
Patent number
US06090852

Reaction notes

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