1,2-Ethanedithiol → HCID 86645389, compound

HRID 925257Notes

Reaction equation

HRID 925257 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH2:10][O:11][C:12](=[O:14])[CH3:13])=[CH:4][CH:3]=1.[CH2:16]([SH:19])[CH2:17][SH:18].[OH-].[Na+]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:9][CH2:10][O:11][C:12](=[O:14])[CH3:13])[S:19][CH2:16][CH2:17][S:18]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 109021,2-EthanedithiolHCID 14798Sodium HydroxideHCID 67521261HCID 67521261, compound

Product 1

HCID 86645389HCID 86645389, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of acetic acid [3-(4-fluorophenyl)-3-oxo-propyl]ester (2.0 g, 9.52 mmol) in dry dichloromethane (40 ml) are added 1,2-ethanedithiol (1.79 g, 19.0 mmol) and boron trifluoride diethyl ether complex (0.68 g, 4.76 mmol) at 0° C. The resulting reaction mixture is stirred at RT for 16 h. After completion of reaction, the mixture is neutralized with 10M aqueous sodium hydroxide and extracted with DCM (3×100 ml). The combined organic layers are washed with water (100 ml), brine (100 ml), dried over anhydrous sodium sulfate and evaporated in vacuo to get the crude, which is purified by column chromatography (silica gel, 5% ethyl acetate/hexane) to yield acetic acid 2-[2-(4-fluorophenyl)-[1,3]dithiolan-2-yl]-ethyl ester (1.80 g, 6.29 mmol, 66%).

Workup

  1. customThe resulting reaction mixture
  2. customAfter completion of reaction
  3. extractionextracted with DCM (3×100 ml)
  4. washThe combined organic layers are washed with water (100 ml), brine (100 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated in vacuo
  7. customto get the crude, which
  8. customis purified by column chromatography (silica gel, 5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ae9cee90a3d849b8b38d649f0af75e2b
Source dataset
uspto-grants-2016_03
Patent number
US09284286B2

Reaction notes

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