(Diethylamino)sulfur trifluoride → HCID 46180112, compound

HRID 433126Notes

Reaction equation

HRID 433126 reaction equation
C(N(S(F)(F)[F:7])CC)C.[C:10]([O:13][CH2:14][CH2:15][CH2:16][CH:17](O)[CH2:18][CH2:19][CH2:20][O:21][C:22](=[O:24])[CH3:23])(=[O:12])[CH3:11]>C(Cl)Cl.C(OCC)(=O)C>[C:10]([O:13][CH2:14][CH2:15][CH2:16][CH:17]([F:7])[CH2:18][CH2:19][CH2:20][O:21][C:22](=[O:24])[CH3:23])(=[O:12])[CH3:11]

Participants

5

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 46180111HCID 46180111, compound

Product 1

HCID 46180112HCID 46180112, compoundYield 94.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (diethylamino)-sulfur trifluoride (571 mg, 3.54 mmol) in CH2Cl2 was added the solution of acetic acid, 7-acetoxy-4-hydroxy-heptyl ester (403 mg, 1.74 mmol) in CH2Cl2 (10 ml) at −78° C. The resulting mixture was allowed to stir for 15 minutes −78° C., 30 minutes at room temperature and then diluted with ethyl acetate (300 ml). The organic solution was washed with sat. NaHCO3, brine and dried over Na2SO4. Evaporation of the solvent and purification of the residue by column chromatography on silica gel, using 15% ethyl acetate in hexanes, gave the title compound (386 mg, 94%) as a colorless oil.

Workup

  1. washThe organic solution was washed with sat. NaHCO3, brine
  2. dry with materialdried over Na2SO4
  3. customEvaporation of the solvent and purification of the residue by column chromatography on silica gel

Sources & evidence

ORD record
ord-3bd57490013b4d3896f321c122f63d98
Source dataset
uspto-grants-2003_12
Patent number
US06667320B2

Reaction notes

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