(R)-(+)-3-Chlorostyrene oxide → HCID 69058624, compound

HRID 1823080Notes

Reaction equation

HRID 1823080 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:6][CH:5]=1.[Cl:18][C:19]1[CH:20]=[C:21]([C@@H:25]2[CH2:27][O:26]2)[CH:22]=[CH:23][CH:24]=1>C(O)C>[Cl:18][C:19]1[CH:20]=[C:21]([C@@H:25]([OH:26])[CH2:27][NH:1][CH2:2][CH2:3][C:4]2[CH:5]=[CH:6][C:7]([S:10][C:11]3[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=3)=[CH:8][CH:9]=2)[CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 10898919(R)-(+)-3-Chlorostyrene oxideHCID 22171376HCID 22171376, compound

Product 1

HCID 69058624HCID 69058624, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-[[4-(2-Aminoethyl)phenyl]thio]phenol (295 mg) and (2R)-2-(3-chlorophenyl)oxirane (186 mg) in ethanol (3.5 ml) was refluxed for 6 hours. The mixture was evaporated. The residue was purified by column chromatography on silica gel (chloroform/methanol=100/3) to give 4-[[4-[2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]ethyl]phenyl]thio]phenol (155 mg).

Workup

  1. customThe mixture was evaporated
  2. customThe residue was purified by column chromatography on silica gel (chloroform/methanol=100/3)

Sources & evidence

ORD record
ord-d43309bcbe5d4a94aa31ac8f146e9e40
Source dataset
uspto-grants-2006_05
Patent number
US07037938B2

Reaction notes

Loading…