Sodium hydride → HCID 19700280, compound

HRID 861845Notes

Reaction equation

HRID 861845 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]([C:9]1[CH:14]=[C:13]([C:15]([C:21]([F:24])([F:23])[F:22])([OH:20])[C:16]([F:19])([F:18])[F:17])[CH:12]=[C:11]([C:25]([C:31]([F:34])([F:33])[F:32])([OH:30])[C:26]([F:29])([F:28])[F:27])[CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].[H-].[Na+].[H-].[CH:40]([C:43]1[CH:48]=[CH:47][C:46]([S:49](Cl)(=[O:51])=[O:50])=[CH:45][CH:44]=1)([CH3:42])[CH3:41]>CN(C=O)C.C(OCC)(=O)C>[F:1][C:2]([F:35])([F:36])[C:3]([C:9]1[CH:14]=[C:13]([C:15]([C:16]([F:18])([F:17])[F:19])([O:20][S:49]([C:46]2[CH:47]=[CH:48][C:43]([CH:40]([CH3:42])[CH3:41])=[CH:44][CH:45]=2)(=[O:51])=[O:50])[C:21]([F:22])([F:23])[F:24])[CH:12]=[C:11]([C:25]([C:31]([F:32])([F:33])[F:34])([O:30][S:49]([C:46]2[CH:47]=[CH:48][C:43]([CH:40]([CH3:42])[CH3:41])=[CH:44][CH:45]=2)(=[O:51])=[O:50])[C:26]([F:29])([F:28])[F:27])[CH:10]=1)([O:8][S:49]([C:46]1[CH:47]=[CH:48][C:43]([CH:40]([CH3:42])[CH3:41])=[CH:44][CH:45]=1)(=[O:51])=[O:50])[C:4]([F:7])([F:6])[F:5]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 166653HydrideHCID 27348824-(Propan-2-yl)benzene-1-sulfonyl chlorideHCID 14384432HCID 14384432, compound

Product 1

HCID 19700280HCID 19700280, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

4.5 g (7.88 mmol) of 1,3,5-tris-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethylethyl)-benzene were dissolved in 40 ml of dry DMF, and 0.95 g (31.5 mmol) of sodium hydride was added while flushing with nitrogen. After dissolution of the hydride, 6.56 g (30 mmol) of 4-isopropylbenzenesulfonyl chloride were added at 0 to 5° C. Slight evolution of heat was observed. The mixture was stirred for 20 hours at 5° C., ethyl acetate was added and the mixture was washed with water, dried, filtered and evaporated down. 9.6 g of crude product were obtained, and said crude product was eluted over a silica gel column with a 1:1 mixture of methylene chloride/hexane. The third fraction obtained was freed from the solvent and gave 6.8 g of 1,3,5-tris-[2,2,2-trifluoro-1-(4-isopropylbenzenesulfonyloxy)-1-trifluoromethylethyl]-benzene. M.p. 105° C.

Workup

  1. customwhile flushing with nitrogen
  2. additionwere added at 0 to 5° C
  3. temperatureSlight evolution of heat
  4. washthe mixture was washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated down
  8. custom9.6 g of crude product were obtained
  9. washwas eluted over a silica gel column with a 1:1 mixture of methylene chloride/hexane
  10. customThe third fraction obtained

Sources & evidence

ORD record
ord-7471434c78dd4aedabd7dd1868a3649f
Source dataset
uspto-grants-1998_02
Patent number
US05716756

Reaction notes

Loading…