(Diethylamino)sulfur trifluoride → HCID 59626056, compound

HRID 2365368Notes

Reaction equation

HRID 2365368 reaction equation
O[CH:2]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1)[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.CCN(S(F)(F)[F:29])CC>C(Cl)Cl>[F:29][CH:2]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1)[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 59626058HCID 59626058, compound

Product 1

HCID 59626056HCID 59626056, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 63c (0.97 mmol, 300 mg) in CH2Cl2 was added DAST (1.015 mmol, 0.133 mL) dropwise at −78° C. under N2. The reaction was kept at −78° C. for 30 min and then quenched with aqueous NaHCO3 solution at low temperature. Additional CH2Cl2 was added to the reaction and the organic solution was concentrated. The crude material was purified flash column chromatography (silica gel, 10% EtOAc/hexanes) to give 63d.

Workup

  1. customquenched with aqueous NaHCO3 solution at low temperature
  2. additionAdditional CH2Cl2 was added to the reaction
  3. concentrationthe organic solution was concentrated
  4. customThe crude material was purified flash column chromatography (silica gel, 10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d06e75a000b6419fb65cfb0930e0a918
Source dataset
uspto-grants-2014_04
Patent number
US08697684B2

Reaction notes

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