Boron trifluoride etherate → Diethyl-4-(mercaptomethyl)-1,3-dithiolane-2,2-dipropanoate

HRID 1650242Notes

Reaction equation

HRID 1650242 reaction equation
[SH:1][CH2:2][CH:3]([SH:6])[CH2:4][SH:5].O=[C:8]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][CH2:9][C:8]1([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[S:6][CH:3]([CH2:4][SH:5])[CH2:2][S:1]1)[CH3:15]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 784951,2,3-PropanetrithiolHCID 80592Diethyl 4-oxoheptanedioate

Product 1

HCID 14405949Diethyl-4-(mercaptomethyl)-1,3-dithiolane-2,2-dipropanoateYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 1,2,3-trimercaptopropane (10.0 g, 0.071 mol) and diethyl 4-oxopimelate (16.43 g, 0.071 mol) in methylene chloride (300 ml) under nitrogen atmosphere was treated with boron trifluoride etherate (2 ml). After stirring for 3 days at room temperature, the reaction was quenched by addition of 200 ml of 5% sodium 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 5% ethyl acetate/hexane as eluent to give 10 g (40%) of the title compound as an oil.

Workup

  1. customthe reaction was quenched by addition of 200 ml of 5% sodium 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 5% ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-93d2fbe2a42748b5a7881207d53df150
Source dataset
uspto-grants-1990_05
Patent number
US04923891

Reaction notes

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