Diethylamine → HCID 21968634, compound

HRID 1107870Notes

Reaction equation

HRID 1107870 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:11]([C@H:12]([OH:24])[CH2:13]S(C3C=CC(C)=CC=3)(=O)=O)=[CH:10][CH:9]=[CH:8][C:5]=2[C:6]=1[CH3:7].[CH2:25]([NH:27][CH2:28][CH3:29])[CH3:26]>>[CH3:1][C:2]1[O:3][C:4]2[C:11]([C@H:12]([OH:24])[CH2:13][N:27]([CH2:28][CH3:29])[CH2:25][CH3:26])=[CH:10][CH:9]=[CH:8][C:5]=2[C:6]=1[CH3:7]

Participants

3

Reactant 2

HCID 8021DiethylamineHCID 21968637HCID 21968637, compound

Product 1

HCID 21968634HCID 21968634, compoundYield 527.3%

Procedure

15 g (41.65 mmol) of (+)-2,3-dimethyl-7-(2-para-methylphenylsulphonyl-1(S)-hydroxyethyl)benzofuran and 210 ml (2.03 mol) of diethylamine are introduced into a 500 ml three-necked flask equipped with a stirrer and a reflux condenser. The solution is stirred at reflux for 16 h and the solution is concentrated. The residue is purified by successive column chromatography operations (elution solvent: 90/10 dichloromethane/methanol) and dried in a desiccator under vacuum over phosphorus pentoxide. 57.4 g of (+)-2,3-dimethyl-7-(2-diethylamino-1(S)-hydroxyethyl)benzofuran are obtained in the wax form -[α]D20 =+94.7° (c=1, methanol). The enantiomeric excess is 98.5%.

Workup

  1. customequipped with a stirrer and a reflux condenser
  2. temperatureat reflux for 16 h
  3. concentrationthe solution is concentrated
  4. customThe residue is purified by successive column chromatography operations (elution solvent: 90/10 dichloromethane/methanol)
  5. dry with materialdried in a desiccator under vacuum over phosphorus pentoxide

Sources & evidence

ORD record
ord-abd47c7797414ea4827047318054b145
Source dataset
uspto-grants-2000_05
Patent number
US06063810

Reaction notes

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