Water → HCID 54570539, compound

HRID 1612621Notes

Reaction equation

HRID 1612621 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:26])[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.[BH4-].[Na+].O>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([OH:26])[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:14][CH:13]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydride2×HCID 53792274HCID 53792274, compound

Product 1

HCID 54570539HCID 54570539, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(4-methoxyphenyl)-3-(4-phenylmethylaminophenyl)-1-oxoprop-2-ene (13.7 g, 0.04 mol) was dispersed in methanol (100 ml). Sodium borohydride (4.1 g, 0.11 mol) was added slowly at ambient temperature under vigorous stirring. After completion of the addition of sodium borohydride, the reaction mixture was kept stirred at ambient temperature for 20 hours. When the reaction was complete, the reaction mixture was poured into water (500 ml), and extracted with toluene. The toluene was removed using a rotary evaporator leaving an oily residue. The crude product was purified from petroleum ether : toluene (9:1 v/v) to give 1-(4-methoxyphenyl)-3-(4-phenylmethylaminophenyl)prop-2-en-1-ol as an amorphous solid in a yield of 12.3 g (89.1% of theory).

Workup

  1. extractionextracted with toluene
  2. customThe toluene was removed
  3. customa rotary evaporator
  4. customleaving an oily residue
  5. customThe crude product was purified from petroleum ether : toluene (9:1 v/v)

Sources & evidence

ORD record
ord-c2807cdb642c42f0ae423c21b2633267
Source dataset
uspto-grants-1993_03
Patent number
US05190909

Reaction notes

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