Thionyl Chloride → HCID 21845927, compound

HRID 619794Notes

Reaction equation

HRID 619794 reaction equation
[Na+].[CH:2]1[C:15]2[C:6](=[C:7]3[C:12](=[CH:13][CH:14]=2)[CH2:11][CH2:10][CH2:9][CH2:8]3)[CH:5]=[C:4]([S:16]([O-:19])(=O)=[O:17])[CH:3]=1.S(Cl)([Cl:22])=O>CN(C=O)C>[CH:2]1[C:15]2[C:6](=[C:7]3[C:12](=[CH:13][CH:14]=2)[CH2:11][CH2:10][CH2:9][CH2:8]3)[CH:5]=[C:4]([S:16]([Cl:22])(=[O:19])=[O:17])[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 87373359HCID 87373359, compound

Product 1

HCID 21845927HCID 21845927, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
60 °C

Procedure

5,6,7,8-Tetrahydrophenanthrene-3-sulfonic acid sodium salt (1 g, 3.68 mmol) is suspended in 5 mL of thionyl chloride. DMF (2 drops) is added and the solution is heated to 60° C. for 30 minutes. After this time, the reaction mixture is concentrated. The residue is triturated with CH2Cl2 and the resulting solid is filtered off. The collected organic solution is concentrated. The crude product is purified by column chromatography eluting with 10% EtOAc/hexanes to give the title compound (0.60 g, 2.3 mmol) as a white solid.

Workup

  1. concentrationAfter this time, the reaction mixture is concentrated
  2. customThe residue is triturated with CH2Cl2
  3. filtrationthe resulting solid is filtered off
  4. concentrationThe collected organic solution is concentrated
  5. customThe crude product is purified by column chromatography
  6. washeluting with 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-426fedda234840bcb70bb7150734bdbe
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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