1,3-Propanedithiol → HCID 86611509, compound

HRID 2108317Notes

Reaction equation

HRID 2108317 reaction equation
O.[F:2][C:3]([F:19])([C:9](=O)[C:10]([F:17])([F:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:20]([SH:24])[CH2:21][CH2:22][SH:23]>C(Cl)Cl>[S:23]1[CH2:22][CH2:21][CH2:20][S:24][C:9]1([C:10]([F:17])([F:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:3]([F:19])([F:2])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 80131,3-PropanedithiolHCID 86616587HCID 86616587, compound

Product 1

HCID 86611509HCID 86611509, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 12.1 mmol of the product of Example 6 in 50 mL of methylene chloride and cool in an ice/water bath under argon. Add 6 g of powdered activated 3A molecular sieves, 18.2 mmol of 1,3-propanedithiol, and then 2.4 mmol of BF3Et2O. Stir for 18 h in the cold, then filter the reaction, washing with ether. Add 100 mL of ether and wash with saturated sodium bicarbonate, water, and brine, and dry over MgSO4. Purify by silica gel chromatography using ether/hexane as eluant to yield the title compound.

Workup

  1. temperaturecool in an ice/water bath under argon
  2. filtrationthen filter
  3. customthe reaction
  4. washwashing with ether
  5. additionAdd 100 mL of ether
  6. washwash with saturated sodium bicarbonate, water, and brine
  7. dry with materialdry over MgSO4
  8. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-d3cc8a8d5e9e44ff96f0c68db1bcf631
Source dataset
uspto-grants-2009_04
Patent number
US07514068B2

Reaction notes

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