(Diethylamino)sulfur trifluoride → HCID 59191387, compound

HRID 1023926Notes

Reaction equation

HRID 1023926 reaction equation
[F:1][C:2]([F:22])([F:21])[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[N:13]=2)=[C:7]([O:19][CH3:20])[CH:6]=1)O.CCN(S(F)(F)[F:29])CC>ClCCl>[F:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([O:11][C:8]2[CH:9]=[CH:10][C:5]([CH:3]([F:29])[C:2]([F:22])([F:21])[F:1])=[CH:6][C:7]=2[O:19][CH3:20])[N:13]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 59191306HCID 59191306, compound

Product 1

HCID 59191387HCID 59191387, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,2,2-trifluoro-1-{4-[(6-fluoropyridin-2-yl)oxy]-3-methoxyphenyl}ethanol (0.22 mmol; 70 mg) under argon in dichloromethane (2 mL) at −78° C. was added dropwise DAST (0.22 mmol; 29 μl). The reaction mixture was let come back to rt for 2 h and quenched with brine (3 ml). The aqueous phase was collected, neutralized with sodium bicarbonate and extracted twice with chloroform. The organic phases were combined, dried over MgSO4, concentrated and purified by preparative TLC on silica gel (ethyl acetate/cyclohexane—30/70) to yield the title compound (25 mg; 0.08 mmol; 37%).

Workup

  1. customquenched with brine (3 ml)
  2. customThe aqueous phase was collected
  3. extractionextracted twice with chloroform
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custompurified by preparative TLC on silica gel (ethyl acetate/cyclohexane—30/70)

Sources & evidence

ORD record
ord-8931087a4f434021b4553944b315aa1d
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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