Boron trifluoride etherate → HCID 86645389, compound

HRID 1925534Notes

Reaction equation

HRID 1925534 reaction equation
[CH2:1]([SH:4])[CH2:2][SH:3].B(F)(F)F.CCOCC.[C:14]([O:17][CH2:18][CH2:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)=O)(=[O:16])[CH3:15].CCCCCC.CC(=O)OCC>C(Cl)Cl>[C:14]([O:17][CH2:18][CH2:19][C:20]1([C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[S:4][CH2:1][CH2:2][S:3]1)(=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 109021,2-EthanedithiolHCID 21226206Ethyl acetate hexaneHCID 67521261HCID 67521261, compound

Product 1

HCID 86645389HCID 86645389, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.79 g (19.0 mol) of ethane-1,2-dithiol and 680 mg (4.76 mmol) of boron trifluoride etherate were added in succession at 0° C. to a solution of 2.0 g (9.5 mmol) of 3-(4-fluorophenyl)-3-oxopropyl acetate in DCM (40 ml). The mixture was then stirred for 16 h at RT and subsequently neutralized with a 10M aq. NaOH sol. Extraction with DCM (3×100 ml) was then carried out and the combined organic phases were washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. CC (hexane/EA 24:1) of the residue yielded 1.8 g (6.3 mmol, 66%) of 2-(2-(4-fluoro-phenyl) -1,3-dithiolan-2-yl)ethyl acetate.

Workup

  1. extractionsubsequently neutralized with a 10M aq. NaOH sol. Extraction with DCM (3×100 ml)
  2. washthe combined organic phases were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd49e0bb7ce14f3393d46dd3b6099d21
Source dataset
uspto-grants-2012_05
Patent number
US08178684B2

Reaction notes

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