Dimercaprol → HCID 14405953, compound

HRID 1383151Notes

Reaction equation

HRID 1383151 reaction equation
[SH:1][CH:2]([CH2:5][SH:6])[CH2:3][OH:4].[C:7]([O:14][CH2:15][CH3:16])(=[O:13])[CH2:8][CH2:9][C:10]([CH3:12])=O.B(F)(F)F.CCOCC>C(Cl)Cl>[SH:6][CH2:5][CH:2]1[CH2:3][O:4][C:10]([CH3:12])([CH2:9][CH2:8][C:7]([O:14][CH2:15][CH3:16])=[O:13])[S:1]1

Participants

5

Reactant 3

HCID 3080DimercaprolHCID 8000Boron trifluoride etherateHCID 10883Ethyl levulinate

Product 1

HCID 14405953HCID 14405953, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 2,3-dimercapto-1-propanol (20.0 g, 0.161 mol) and ethyl levulinate (22 g, 0.161 mol) in methylene chloride (600 ml) under a nitrogen atmosphere was treated with boron trifluoride etherate (5 ml). After stirring for 3 days at room temperature, the reaction was quenched by addition of 250 ml of 5% potassium bicarbonate solution. The organic phase was separated and dried over anhydrous sodium sulfate. The drying agent was filtered and the filtrate concentrated on the rotary evaporator. The residue was chromatographed on silica gel using 6% ethyl acetate/hexane as eluent to give 17 g (43%) of the title compound as an oil.

Workup

  1. customthe reaction was quenched by addition of 250 ml of 5% potassium bicarbonate solution
  2. customThe organic phase was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe drying agent was filtered
  5. concentrationthe filtrate concentrated on the rotary evaporator
  6. customThe residue was chromatographed on silica gel using 6% ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-79e72c26fb1849feb23e6046267cdfc0
Source dataset
uspto-grants-1989_02
Patent number
US04808729

Reaction notes

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