Lipoic acid → 5-(1,2-Dithiolan-3-YL)pentanoyl chloride

HRID 870284Notes

Reaction equation

HRID 870284 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]1[C@@H:9]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)[S:8][S:7][CH2:6]1>C(Cl)Cl>[S:7]1[CH2:6][CH2:5][CH:9]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([Cl:3])=[O:16])[S:8]1

Participants

4

Reactant 2

HCID 6112Lipoic acidHCID 24386Thionyl Chloride

Product 1

HCID 579942155-(1,2-Dithiolan-3-YL)pentanoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of thionyl chloride (1.4 mL, 7.5 mmol) in CH2Cl2 (30 ml) at 0° C. was added a solution of lipoic acid (3.0 g, 5 mmol), dissolved in dichloromethane, dropwise over 1 h. The mixture was allowed to stir for additional 3 h. at the same temperature. After completion of the reaction the solvent was removed under vacuum using a dry-ice collection trap being very careful not to heat the reaction mixture since this will decompose the product. Reaction proceeds with quantitative yield.

Workup

  1. customAfter completion of the reaction the solvent
  2. customwas removed under vacuum
  3. customa dry-ice collection trap
  4. temperatureto heat the reaction mixture since
  5. customReaction

Sources & evidence

ORD record
ord-7db339e89ef343b4a22a7d0cf2e8d423
Source dataset
uspto-grants-2015_03
Patent number
US08969549B2

Reaction notes

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